About The Role

As Headway works to build a new mental healthcare system that everyone can access, we’re facing unique operational challenges and opportunities that come with growing and scaling at an unparalleled rate. We’re pushing the boundaries of the existing healthcare system so that we can fulfill our promise to providers, patients, and payers to create access to high quality providers across the nation. In order to do that, we’re building a world class operations team that enables efficiency, growth, and quality, and as a member of this team, you will have the opportunity to have a material impact on the trajectory of Headway and help define a function core to the livelihood of our business and the impact we deliver for our partners and clients.

As a Business Operations Lead, you will drive complex, cross-functional initiatives that advance pod-level objectives. You'll work independently to identify opportunities, address dependencies, and ensure alignment across stakeholders - turning ambiguous problems into structured analyses, scalable processes, and clear recommendations. You'll bring analytical rigor to root-cause investigations, design workflows and tooling that improve efficiency and reliability, and own initiatives end-to-end from scoping through delivery. This role requires strong problem-solving skills, a builder's mindset toward operational design, and the ability to coordinate across teams to drive measurable outcomes.

What you’ll do at Headway

• Drive complex, cross-functional initiatives that advance pod-level objectives - identifying opportunities, addressing dependencies, and ensuring alignment across stakeholders.
• Build and operate scalable workflows and processes (0→1) that improve efficiency, reliability, and throughput across your domain.
• Leverage data tools to extract insights, validate assumptions, and inform decisions, synthesizing findings into clear recommendations that guide pod and organizational priorities.
• Plan, execute, and deliver initiatives end-to-end by setting clear objectives, timelines, and success metrics – driving accountability across functions without formal authority.

You’ll be great for this role if you:

• You have 5-7 years of experience in operational roles at high-growth companies; background in consulting, finance, or business operations preferred but not required.
• You independently deconstruct complex problems into structured, testable components - and you're comfortable working through ambiguity without waiting for full clarity.
• You're proficient with AI & data tools (e.g., Looker, Excel, SQL, dashboards) and use them fluently to extract insights, validate assumptions, and streamline workflows.
• You design systems with scale in mind - anticipating bottlenecks, iterating based on feedback, and codifying learnings into playbooks and standards.
• You coordinate resources and align priorities across teams, building trust through transparency, accountability, and clear communication.
• You take calculated risks and make decisions that advance pod objectives, anticipating downstream impacts before taking action.
• You're motivated by the opportunity to make an impact on one of our generation's defining problems: affordable mental healthcare.

Compensation and Benefits:

The expected base pay range for this position is $105,400 - $155,000 based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About the Team & Role

• Headway is building the infrastructure for mental healthcare to work for everyone. Our CX Workforce Management (WFM) team is the staffing engine of that operation—connecting patients, providers, and payers through a contact center that is rapidly expanding in scope and headcount.
• We are looking for a highly technical Capacity Planning Lead to own the demand-and-supply modeling that drives our hiring plans, headcount strategy, and budgetary decisions with leadership.

You Will

• Architect the Capacity Engine: Build and maintain a comprehensive capacity model. You will mathematically map volume mix, omnichannel routing (Chat/Email/Voice), offshore capture rates, customer escalations, the rate of cross-functional (XFN) holds, and more.
• Model Agent Productivity: Transform raw agent-level workforce data into actionable intelligence. Compute ticket lifecycle metrics, validate handle time distributions and the number of interactions required to resolve an issue. Build logic to detect outlier behaviors (e.g., cherry-picking, complexity-driven variance) and support operational leaders as a data insights lighthouse using AI tools.
• Own the Financial Translation: Bridge the gap between Operations and Finance. Translate Erlang C FTE requirements into a fully loaded staffing plan, actively participating in monthly Budget reconciliation meetings to explain volume and handle-time variances in dollar terms.
• Drive BPO Capacity Locks: Generate and enforce the 30-60-90 day headcount lock plans for our offshore vendor partners, holding them accountable to forecasted hiring and shrinkage targets.
• Own the Staffing Plan: Compute, align, and project operational rates down to the customer’s issue-type level and market segment. Apply seasonality adjustments and project demand across monthly, quarterly, and multi-year horizons.
• Translate Messy Reality into Clean Data: Map raw ticket data through complex carrier → payer → agent specializations, handling the structural messiness of real-world insurance routing and triage misclassifications. Highly organized and with attention to details. 

You’d be a great fit if…

• WFM & Queue Physics: You possess a deep understanding of capacity planning fundamentals. You know exactly how Volume, AHT, and other KPIs – like Reopen Rate – translates to required agent-minutes, and how shrinkage, attrition, occupancy, and SLA targets layer on top.
• Cross-Functional Influence: You don’t just forecast the weather; you help build the roof. You have a track record of taking capacity insights (e.g., "This specific billing intent is breaking our Chat concurrency") and partnering with Product and Engineering to drive automated deflection.
• Data-Backed Storytelling: You communicate with CX leadership and Finance using clear, opinionated, data-backed narratives–avoiding overly technical language.
• AI-Augmented Execution: You have experience leveraging LLMs and AI-assisted tooling to accelerate exploratory data analysis, and iterate on models. Crucially, you possess the analytical rigor to know when to trust the AI's output and when to verify it.

Advanced SQL Fluency: You are highly comfortable in Snowflake (or similar SQL dialects), writing complex queries utilizing CTEs, window functions, and UNION ALL orchestration. You think in DAGs and data pipelines, not just spreadsheets.

Compensation and Benefits:

The expected base pay range for this position is $124,100 - $146,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

We're looking for a Director of Clinical Excellence and Education to own network oversight and build and scale Headway's provider education programs. In this role, you will establish the strategy, infrastructure, and content that empower therapists, psychologists, and psychiatric prescribers in Headway's network to deliver exceptional care while fostering trust and transparency among the provider community.

Headway's provider network has grown rapidly, and with that growth comes an opportunity to invest deeply in the clinicians who make our mission possible. You would join as the leader of this function, to bring visibility to the health of the network and shape how Headway educates, supports, and upskills tens of thousands of mental health providers across the country. Given the scale of the Headway provider network, under your leadership, we have the opportunity to be a national leader in Mental Health Provider Education. 

You will own the end-to-end clinical education strategy in partnership with Clinical, Product, and Growth leadership at Headway. You will design and deliver clinical excellence programs and scalable learning experiences, from continuing education curricula and onboarding programs to peer learning communities and practice-building resources. You will manage the learning management system (LMS) and community platforms that underpin this work. Your programs will measurably improve provider engagement, clinical quality, and retention across Headway's network. You will also help ensure the visibility and integrity of Headway's provider network by tracking key indicators of network health and driving clinical excellence and education programs that reinforce clinical standards, documentation quality, and regulatory compliance.

This role requires deep clinical credibility, expertise in adult learning, and the ability to build systems that scale. You will collaborate closely with stakeholders across Clinical, Product, Engineering, Operations, Marketing, Growth, and Data. You'll have a chance to directly shape how Headway supports its providers. Externally, you will engage with leading voices in mental health education, professional development, and provider community building.

This is a unique opportunity to combine clinical expertise, education design, and community leadership at a company that is transforming access to mental health care.

You Will:

• Monitor and ensure the visibility and integrity of Headway's provider network by tracking key indicators of network health — including provider competency, compliance, and clinical quality — and maintaining clear organizational sight lines into network performance at scale
• Expand and lead the clinical education function: define the vision, develop quarterly roadmaps, secure resources, and oversee end-to-end execution of all provider education initiatives
• Develop targeted education and remediation programs that upskill Headway's 60,000+ providers on clinical standards, documentation quality, and regulatory compliance — translating network health insights into structured learning interventions that continuously raise the bar for care delivery
• Design and curate scalable learning experiences across the full provider lifecycle — clinical onboarding, continuing education (CE/CME), evidence-based practice training, documentation and billing education, and specialty skill-building curricula — developed in partnership with internal clinical experts and external thought leaders
• Manage the LMS and community platforms that serve Headway's provider network, ensuring seamless content delivery, learner tracking, credentialing, and engagement analytics at scale
• Support a connected provider community through educational programming (webinars, town halls, peer learning), and serve as an internal subject matter expert for provider-facing communications across teams
• Establish and own education KPIs — including engagement, learning outcomes, provider satisfaction, and clinical quality improvement — using data to continuously iterate on programs and partnering with the Research team to identify opportunities to publish on provider and patient outcomes
• Partner cross-functionally and influence senior leadership — work with Product, Engineering, Operations, and Marketing to embed education into the provider experience; make the case for resources that drive provider engagement, satisfaction, and clinical excellence; and navigate ambiguity in defining scope, success criteria, and long-term vision as this function scales

You would be a great fit if you have:

• Actively licensed as a therapist, clinical psychologist, Nurse Practitioner (PMHNP-BC), or psychiatrist (MD/DO) with 10+ years of clinical experience in mental health settings
• Deep expertise in clinical education and adult learning. You have designed, delivered, and scaled training programs for clinicians, with a strong understanding of instructional design principles, competency-based education, and CE/CME accreditation processes
• Hands-on experience with learning management systems (LMS). You have evaluated, implemented, and managed platforms (e.g., Docebo, Intellum, Canvas, Tovuti, or similar), including content authoring, learner tracking, and integration with other systems
• Experience in a high-growth health care, health tech, or digital health environment. You understand the unique challenges of supporting a large, distributed provider network and can build programs that scale
• Strong data orientation and experience building measurable systems. You use quantitative and qualitative data to measure program effectiveness, inform content strategy, and demonstrate ROI to leadership. Comfort with analytics tools (e.g., Looker, spreadsheets, survey platforms) is expected
• Experience partnering with cross-functional teams across product, engineering, operations, and marketing to integrate education and community into the broader provider experience
• Exceptional communication and stakeholder management skills, able to translate clinical and educational concepts for technical and business audiences, and to represent Headway credibly to external clinical communities
• Comfort with ambiguity and a builder's mindset. You thrive when creating something new, can prioritize ruthlessly, and are energized by the opportunity to define a function rather than inherit one

Compensation and Benefits:

The expected base pay range for this position is $170,000- $265,000 based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About the role:

At Headway, we’re building the largest national network of therapists who accept insurance — and making mental healthcare radically more accessible in the process. Our ability to serve patients starts with providers. As Director of Product for Provider Growth, you’ll lead the product vision, strategy, and execution for how we attract, onboard, and activate providers on Headway. 

Your mission is to grow the number of active providers on Headway by delivering a seamless, delightful onboarding and activation experience and by building high-impact growth channels. You’ll lead cross-functional teams responsible for critical surfaces across the provider funnel, including leads forms intakes, credentialing, onboarding, and referrals programs. You’ll also drive new product surfaces and big bets that tie into long-tail growth opportunities, like growing Group Practices. 

Provider growth is one of Headway’s most important levers for scaling access to affordable mental healthcare. Whether it's building a world-class referrals engine, optimizing conversion through onboarding, or laying the groundwork for future market expansion, this role is at the heart of Headway’s growth story — and critical to advancing our mission. This is a pivotal role for both Headway and our mission to make mental healthcare more accessible.

What you’ll do at Headway:

• Own the vision and strategy for provider growth — balancing bold bets with near-term impact to increase the number of new activated providers.
• Collaborate deeply with cross-functional teams — design, engineering, data, operations, GTM — to learn fast, ship often, and deliver meaningful outcomes.
• Lead and scale a team of PMs focused on improving conversion through onboarding, referrals, and provider activation flows.
• Use data and design to optimize the onboarding journey and improve conversion, provider experience, and overall efficiency.
• Stay close to providers and the market, using insights, data, and feedback to inform product strategy and prioritization.
• Be a strategic thought partner across the company on growth, activation, and provider experience.

You’ll be great for this role if you:

• Are a growth-minded product leader with 8+ years of experience driving measurable business impact through product innovation, with at least 4 years managing PMs.
• Have experience with B2B2C or platform products, ideally in a growth, marketplace, or onboarding-focused role.
• Are a strategic thinker who can zoom in and out — balancing long-term vision with near-term execution, and being honest about what matters most.
• Love digging into customer insights, data, and operational realities to shape your strategy.
• Thrive in ambiguous, fast-paced environments and excel at bringing clarity, focus, and momentum.
• Are a motivational leader who knows how to build high-performing teams and influence cross-functional stakeholders.
• Care deeply about delivering meaningful impact — for providers, patients, and Headway’s mission.

Compensation and Benefits:

The expected base pay range for this position is $249,600 - $312,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

• Benefits offered include:
• Equity Compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

#LI-AC1

About the Role:

As a Senior Associate on the CX Programs team, you'll play a key role in shaping and improving the customer experience at Headway. You'll act as a CX expert and true voice of the customer: bringing customer needs and pain points into every conversation with cross-functional partners, and turning those insights into better processes, clearer support strategies, and more seamless launches.

In this role, you'll own projects end to end, from identifying gaps to driving solutions that land well for both customers and agents. You'll collaborate closely with teams across the company to ensure consistency in how we support our customers, and you'll use data to influence meaningful improvements to our satisfaction and performance metrics. 

• You Will
• Develop understanding of customer needs and pain points to design, iterate, and improve end-to-end customer experience
• Contribute to the evolution of key KPIs such as CSAT, TTR, and self-resolution improvements for relevant projects
• Support CX change readiness for new features and releases by mapping requirements, developing CX processes, and managing timelines
• Create and enhance support processes to improve customer experience and provide consistency in support strategy execution
• Partner with the Knowledge Management team to ensure ongoing clarity and usability of SOPs
• Support cross-functional teams in implementing customer-centric product and process improvements, driving change to improve CSAT
• Analyze customer feedback and ensure alignment across teams via insight readouts and root cause analysis
• Drive CX enablement by leveraging AI tools to improve team efficiency, reduce resolution times, and scale support operations
• You’d be a great fit if…
• You're deeply curious about the full customer journey and seek to understand the experience beyond what comes through a support ticket
• You can translate messy customer data into clear insights and compelling narratives for cross-functional stakeholders
• You're energized by owning projects end-to-end and thrive in environments where processes are still being built
• You have a point of view on what great customer experience looks like and aren't shy about advocating for the customer when working with Product and Ops teams
• You're excited about using AI tools to work smarter and enable our CX team

Compensation and Benefits:

The expected base pay range for this position is $80,920- $119,000 based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About The Role

Headway is looking for a Systems Lead with a strong background in CX analytics, AI adoption, and voice platform configuration to join our CX Systems team. Our CX team is the tip of the spear delivering affordable mental healthcare to millions — and you'll shape how that experience is measured, automated, and continuously improved.

This is a unique opportunity to own the intersection of data, AI, and voice in a fast-scaling CX organization. You won't just report on what's happening — you'll diagnose root causes, configure the systems that fix them, and drive adoption of the AI tools that help our agents and customers get to resolution faster.

You will: 

• Own CX systems metrics and reporting — design, maintain, and evolve dashboards that track key performance metrics (routing accuracy, system uptime, tool utilization) and translate data into clear operational recommendations for CX leadership
• Lead AI adoption across the CX team — measuring impact rigorously; drive agent adoption through enablement and change management
• Configure and optimize the voice/telephony platform — own IVR design, intelligent call routing, queue management, and voice bot scripting; ensure routing logic reflects current business priorities
• Partner with Engineering, IT, Product, and BPO teams to translate CX business requirements into scalable technical configurations
• Manage end-to-end technical programs — from scoping and vendor alignment through deployment and post-launch measurement
• Proactively identify system, analytics, and process gaps; build the business case and drive improvements from idea to production
• Represent the CX team in cross-functional initiatives and be the go-to expert on CX data, AI tooling, and voice systems

You’d be a great fit if…

• You have 3–5+ years of experience in CX operations, analytics, or systems — ideally with exposure to all three
• You've configured or optimized a voice/telephony platform (IVR, call routing, voice bots) — Five9, Genesys, Twilio, Amazon Connect, or similar
• You're comfortable working with new tools, integrations, and configurations across the CX tech stack (CRM, QA, WFM) and can plug in when needed.
• You've deployed or meaningfully improved an AI tool in a CX context — and have the adoption metrics to prove it
• You're comfortable pulling and presenting data without relying on a dedicated analyst — SQL, Looker, Tableau, Metabase, or similar
• You thrive in ambiguity and move fast without sacrificing quality; you know when to ship and when to wait
• You're an analytical and creative problem solver: you dig into root causes, quantify impact, and build solutions that are elegant enough to scale
• You communicate clearly to both technical and non-technical stakeholders, and know how to influence without formal authority
• You're motivated by making an impact on one of our generation's defining problems — making mental healthcare affordable and accessible

Compensation and Benefits:
The expected base pay range for this position is $99,280-$146,000  based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

As a Strategic Finance Manager, you will sit within the Strategic Finance GTM team and play a critical role in driving durable marketplace health across Provider and Patient. This is a highly cross-functional role for someone who thrives at the intersection of financial analysis and strategic decision-making. You'll build models, track performance, and surface insights that drive appointment volume, retention, and long-run unit economics.

You will:

• Serve as the primary Finance Business Partner for appointments reporting — patient churn, provider churn, appointments per provider, net revenue retention, and active patient behavior
• Build and maintain functional operating models for Provider and Patient, and drive ongoing budgeting and forecasting processes for the function
• Lead deep dives to identify business problems, perform root cause analysis, and develop strategies for accelerating progress — monitoring trends, surfacing early signals of de-averaged performance, and partnering with product, operating, and growth teams to address issues and scale successful behaviors
• Partner cross-functionally to surface insights and support strategic decision-making
• Develop dashboards, reporting, and executive-ready materials to communicate progress against goals

You’d be a great fit if:

• You have 6+ years of professional experience, ideally in a mix of financial services (Investment Banking / Consulting / Private Equity) and highly analytical roles at a fast-growing tech company (Strategic Finance)
• You are highly proficient in Google Sheets (advanced formulas) and Looker (or similar BI tools) and comfortable working with large datasets
• You are detail-oriented and have a “measure twice, cut once” approach when working with financial data
• You are excited about AI and how it's reshaping finance, and you actively explore and apply AI tools to drive faster insights, greater efficiency, and smarter decision-making
• You’re excited to work cross functionally with the business teams to develop a greater understanding of function-specific efficiency metrics and help course-correct where necessary
• You take ownership and are a resourceful self-starter—you proactively seek context, solve ambiguous problems, and anticipate stakeholder needs
• You communicate complex insights clearly, tailoring your message for different audiences (finance vs. business/product partners)
• You thrive in a fast-paced, cross-functional environment and enjoy collaborating with Provider, Patient, product, and growth teams
• You are excited about joining a mission-driven company and driving marketplace efficiency and durable growth to improve mental healthcare access

Compensation and Benefits:

The expected base pay range for this position is $152,000 - $190,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

#LI-LN1

As a Provider Growth Associate (Account Executive), you’ll have an instrumental impact as we expand Headway across the country. You’ll be directly responsible for scaling our community of therapists and psychiatrists in order to increase access to quality care for those who need it. 

As a sales expert in a rapidly scaling environment, you’ll be on the front line of expanding our therapist networks through a full-cycle sales motion. As the first point of contact for prospective providers, you’ll work cross-functionally to translate the insights you glean from your sales process into products and processes that help us execute on our mission.

You'd love this role if: 

• You have 1-3 years experience in consultative sales or consumer sales (bonus points if you’ve done this in a startup environment, or sold to small businesses before)
• You know how to connect with people whether in person, over the phone, or over email
• You have a deep work ethic and the desire to continuously improve 
• You like to be challenged and push yourself to get better every day and in every pitch
• You have thick skin, and are comfortable thinking on your feet, trying new approaches, and bouncing back when things don’t go your way 
• You take a scientific approach to growth, experimenting with a variety of tactics to discover how to generate leads and sell you have the analytical ability to identify which channels warrant more investment, and which we should avoid
• You want to learn and grow. You view this role as an opportunity to learn from a bright and talented team and are excited to take on more responsibility at Headway over time
• You believe in our mission
• You want to work for Headway because you believe in the importance of affordable and accessible mental health care, for everyone

Compensation and Benefits:

• Salary information is based on a single salary target per role and is differentiated based on geographic location.
  • Group A = $77,000 - New York City, San Francisco/Bay Area, Los Angeles / Orange County Area, San Diego, Seattle, Boston, Austin
  • Group B = $69,300 - Chicago, Denver, Washington DC, Philadelphia, Pittsburgh, Atlanta, Nashville, Phoenix, and Portland
• Other compensation includes commission. Commission payments are monthly.
• Benefits offered include:
  • Equity Compensation
  • Medical, Dental, and Vision coverage
  • HSA / FSA
  • 401K
  • Work-from-Home Stipend
  • Therapy Reimbursement
  • 16-week parental leave for eligible employees
  • Carrot Fertility annual reimbursement and membership
  • 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
  • Flexible PTO
  • Employee Assistance Program (EAP)
  • Training and professional development

About the Role

The Recruiting Coordination team is the operational backbone of Headway's talent engine. We're the team that makes hiring happen — from the moment a candidate is scheduled for their first interview to the day an offer is signed. We own the logistics, the details, and the candidate experience that shapes how people feel about Headway before they ever join.

We are looking for a strong partner for our Recruiters and Sourcers to enable an exceptional candidate experience for potential hires across the company. As we continue to scale at hyper-growth pace, we're seeking an operationally excellent and relationship-driven teammate to plug into searches, collaborating effectively with hiring managers, candidates, interview teams, and talent stakeholders. This is a great opportunity for a Talent professional who is looking for exposure to a mission-driven, high growth organization!

You Will

• Schedule and coordinate interviews end-to-end across a portfolio of open roles, ensuring every detail is confirmed and nothing falls through the cracks
• Serve as a primary scheduling point of contact for candidates throughout the interview process, delivering a warm and organized experience
• Maintain accurate candidate records and pipeline data in Greenhouse in real time
• Partner with recruiters and sourcers to manage logistics — calendar coordination, interviewer prep, and video link setup — across multiple simultaneous reqs
• Communicate proactively when schedules change, conflicts arise, or candidates need updates
• Support TA operational workflows, including BrightHire coordination and other tooling as we automate and streamline

You'd Be a Great Fit If…

• You're known for being organized and detail-oriented — you're the person who catches the timezone error before it becomes a problem
• You've worked in a high-volume coordination, scheduling, or operations role and thrived under the load
• You communicate clearly and warmly — candidates and interviewers alike feel informed and taken care of
• You treat data hygiene as a professional standard, not an afterthought
• You're proactive — you don't wait to be asked before flagging a conflict or closing a loop
• You're energized by the pace of a fast-growing company and comfortable with change

Compensation and Benefits:

The expected base pay range for this position is $91,000-$119,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About The Role

At Headway, we're building the future of behavioral health quality and safety. We're hiring a Clinical Quality Manager to support our clinical quality monitoring initiatives and our Ongoing Professional Practice Evaluation Program for our network of NPs and MDs/DOs. You'll work cross-functionally with Operations, Compliance, Product, Engineering, and other teams to build robust clinical quality frameworks and optimize chart review workflows. This is an exceptional opportunity to reimagine how behavioral health quality is defined and measured at a rapidly scaling, mission-driven company.

You will:

• Support our Professional Practice Evaluation programs, directly improving clinical outcomes across our provider network of NPs and MDs/DOs
• Conduct routine chart reviews and monitoring, providing feedback to clinicians and creating remediation plans for documentation concerns and adherence to evidence-based practices
• Collaborate with Operations team to develop automated quality monitoring systems
• Supervise clinical teams and peer reviewers, building clinical oversight capabilities as we scale
• Partner with cross-functional teams to optimize workflows and create scalable feedback systems for providers

You will love this role if:

• You are a licensed psychiatrist (MD/DO) or Psychiatric Mental-Health Nurse Practitioner (PMHNP) with 2+ years of post-graduate experience in both clinical practice and fast-paced business environments
• You have extensive experience completing quality chart reviews and audits for healthcare organizations, with a track record of training others on clinical documentation standards
• You are curious about how AI is transforming clinical practice — you're excited to help evaluate, validate, and shape how new AI tools are deployed responsibly and how they improve care quality at scale.
• You thrive as a collaborator, building bridges between clinical strategy and product, operations, and business teams
• You are a strategic first-principles thinker who can decompose complex problems into clear strategies and actionable plans
• You are motivated by the opportunity to improve access to high-quality behavioral healthcare at scale

Compensation and Benefits:

The expected base pay range for this position is $144,400 - $225,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About the Role

We're hiring an Executive Recruiting Coordinator to own the candidate experience end-to-end across all of our senior and executive level searches. In this role, you will operate as a strategic partner to our Executive Recruiters and Leadership team, ensuring candidates feel taken care of and have a truly remarkable experience interviewing with Headway. You’ll own complex scheduling across multiple senior stakeholders, manage high-touch candidate logistics and ensure we are providing a ‘white glove’ experience every time. 

You Will

• Own interview scheduling end-to-end for all active senior level searches - managing complex, multi-timezone calendars across senior candidates, executives, and cross-functional interview panels
• Serve as the primary coordination point of contact for executive candidates, delivering a warm, polished, and organized experience at every touchpoint
• Maintain real-time accuracy in Greenhouse across all exec pipelines - candidate records, interview stages, and pipeline data
• Build and own the operational playbook for executive coordination - confirmation cadences, prep material delivery, debrief logistics, to ensure the process is consistent and scalable
• Partner closely with senior recruiters to proactively flag scheduling risks, resolve conflicts, and keep searches moving without interruption
• Handle sensitive search details with discretion, representing Headway professionally in every interaction with candidates and hiring leaders

You'd Be a Great Fit If…

• You have 2+ years coordinating executive or senior leadership searches before and understand what makes the candidate experience at that level different
• Your scheduling record is near-perfect - you're the person who catches the timezone error, the double-booking, and the missing confirmation before anyone else notices
• You can independently own a full portfolio of complex searches without daily direction - you know what needs to happen and you make it happen
• You communicate with polish and precision - your emails to VP and C-suite candidates are clear, warm, and professional without being stiff
• You think in systems - when something's inefficient, you don't just work around it, you fix it and document it so it doesn't happen again
• You handle ambiguity and last-minute changes without losing your footing — executive schedules shift constantly, and you stay ahead of it

Compensation and Benefits:

The expected base pay range for this position is $124,000-$146,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About the Role

At Headway, we’re building the largest national network of therapists who accept insurance — and making mental healthcare radically more accessible in the process. Our ability to serve patients starts with providers. As Staff Researcher for Provider Growth, you’ll lead research to inform the product vision, strategy, and execution for how we attract, onboard, and activate providers on Headway. 

In this role, you will be a strategic partner, utilizing a mixed-methods approach to uncover critical insights about our Providers. You will conduct research to inform business, product, and marketing strategies, helping us identify and unlock significant growth and differentiated product opportunities. You’ll be responsible for foundational insights and developing a nuanced understanding of diverse provider segments—practice starters vs. veterans, therapists vs. prescribers, solo vs. group practices—each with different needs, painpoints, and behaviors. You’ll share insights and make recommendations about when to personalize and when to unify, helping the team build solutions that flex to serve unique segment needs while maintaining a coherent, unified Headway experience. You'll operate with high autonomy and ownership, presenting regularly to executive leadership including our CEO and making bold recommendations backed by clear, evidence-driven rationale.

Provider growth is one of Headway’s most important levers for scaling access to affordable mental healthcare. Whether it's building a world-class referrals engine, optimizing conversion through onboarding, or laying the groundwork for future market expansion, this role is at the heart of Headway’s growth story — and critical to advancing our mission. This is a pivotal role for both Headway and our mission to make mental healthcare more accessible.

Core Responsibilities

• Lead end-to-end research projects, from identifying key questions and scoping research plans to conducting the work, synthesizing findings, and presenting actionable recommendations to stakeholders across the business.
• Employ a mixed-methods research skillset, combining quantitative data (surveys, A/B tests, behavioral analytics) with qualitative insights (IDIs, ethnography, concept testing) to develop a comprehensive understanding of how providers source, add, convert, and retain patients.
• Identify and size growth opportunities by analyzing provider behavior, patient sourcing patterns, and competitive dynamics. You will be expected to think critically about what's next for Headway and how we can best build a new mental healthcare system that everyone can access.
• Act as a strategic thought partner to product, design, and marketing teams working on the Provider growth journey, helping them define problem spaces, understand provider segments, and inform the development of new features, products, and campaigns.
• Drive a culture of research and user-centricity across the pod and broader organization by evangelizing findings and promoting a deep understanding of our diverse provider segments and their patients.
• Mentor and provide guidance to junior researchers, helping to build and scale our research practice.

Key Skills and Qualifications

• A PhD + 3 years of industry research experience (ideally with experience in a fast-moving tech environment)
• Or a Masters + 6 years
• Or a Bachelors + 8 years
• Expertise in both qualitative and quantitative research methodologies.
• A demonstrated ability to identify and frame business problems and opportunities, with a portfolio of work that shows direct impact on growth metrics.
• Experience in 0-1 product development.
• Strong analytical and critical thinking skills, with the ability to turn complex data and observations into clear, compelling narratives.
• Excellent communication and presentation skills, with the ability to influence and collaborate with diverse teams—up to and including executive leadership.
• A self-starter who is innately curious about human behavior and passionate about solving complex problems.

Compensation and Benefits:

The expected base pay range for this position is $212,000 - $265,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About This Role:

Every month, hundreds of thousands of patients and providers interact with Headway's support systems. Today, most interactions are handled by human agents working across disconnected tools. We believe CX is a product, not just a department — and the right product leader can transform how Headway supports its customers while dramatically improving both satisfaction and cost efficiency.

As Director of Product for CX, you will build Headway's CX product function from the ground up. You'll own the product vision and strategy for how patients and providers get help — from AI-powered self-resolution to context-aware agent tooling to the feedback loops that connect support insights back to the product.

You will:

• Define the vision and strategy for Headway's CX product — spanning AI-powered resolution, agent tooling, proactive engagement, channel strategy, knowledge systems, and the feedback loops that connect support insights back to the product.
• Build and lead a team of product managers focused on reducing cost-to-serve while increasing resolution quality and customer satisfaction.
• Own the AI resolution layer — build the agentic workflows and API integrations that enable the AI agent to actually resolve problems, not just answer questions. Define the autonomy framework: what AI handles without human involvement, what needs guardrails, and what requires a human.
• Build proactive engagement — systems that contact customers before they discover problems. Shift Headway's CX from reactive to proactive.
• Launch and unify all contact channels — email, text, and voice — with intelligent routing that delivers differentiated experiences based on customer context, value, and issue type.
• Own the knowledge and quality layer — machine-readable SOPs, AI evaluation frameworks and crisis escalation pathways.
• Partner deeply with CX Operations to build agent tooling that makes human agents dramatically more effective — AI copilot, full journey context, auto-generated summaries.
• Close the feedback loop: build the system that identifies the highest-impact product defects driving support volume and surfaces them to insurance platform teams for upstream fixes.
• Establish measurement frameworks that connect CX product investments to business outcomes..

You'd Be a Great Fit If...

• You are a product leader with 8+ years of experience, including at least 3 years managing PMs, with a track record of building CX/support products at scale.
• You have a strong point of view on how AI will transform customer support — and you've shipped AI-powered CX products.
• You've launched or scaled multi-channel CX systems and used intelligent routing for personalized experiences.
• You've demonstrated the ability to simultaneously reduce support costs and improve customer satisfaction.
• You thrive at the intersection of product and operations.
• Nice to have: experience in healthcare, insurance, or other industries with complex customer interactions.

Compensation and Benefits:

The expected base pay range for this position is $249,600 - $312,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About the Team & Role

Mental health care shouldn't come with surprise bills. It shouldn't cost patients hours on the phone to find out what their insurance actually covers, and it shouldn't cost providers sleep wondering whether they'll get paid for the work they did. At Headway, getting insurance right — reliably, accurately, and in real time — is one of the most important problems we solve. And it sits at the heart of a multi-billion-dollar mental health system we're building from the ground up.

We're hiring an Engineering Manager to lead the team that owns Headway's benefits platform: the core systems that determine what every patient's insurance actually covers, what they'll pay out of pocket, and how providers get reimbursed accurately. This is infrastructure that the rest of the company runs on. When it works, millions of appointments happen smoothly; when it doesn't, patients don't get care and providers don't get paid.

You'll lead a team of 4–5 engineers, co-own the roadmap with your PM, and report to our Senior Engineering Manager, who will give you the autonomy to run this team end-to-end while being a close thought partner. This is a role designed for a leader who still wants to be in the weeds — reading PRs, shaping tech specs, showing up to design reviews as a contributor. At Headway, technical credibility is how engineering managers lead.

What You'll Own

• A team of 4–5 engineers — hiring, growing, and coaching them through the most formative stretch of their careers
• A platform that sits at the core of Headway's business — every patient booking, every provider payout, and every claim depends on what your team builds
• The roadmap, in partnership with product — setting the pace, the priorities, and the bets for one of the most leveraged engineering teams at the company
• The technical standards and team culture — how the team scopes work, how it makes architectural decisions, how it responds to incidents, and how it treats on-call as a first-class concern
• A seat at the table — partnering with the leaders of claims, eligibility, billing, and payer partnerships to keep the whole system honest

You'd Be a Great Fit If...

• You built your career as an engineer first. You've spent 5+ years writing and shipping code at a senior or staff level, and you're still close enough to the craft to push back in a design review.
• You're early in your management career — maybe you're already running a small team, or maybe you've been a tech lead with a few reports and you're ready for a bigger scope. We're betting on trajectory, not tenure.
• You've built robust systems and love thinking through all the moving pieces of a complex system. You've owned things other teams depend on, and you take that responsibility seriously.
• You understand deep problems and build intelligent systems with the right leverage — whether that's agents, predictive algorithms, or the rules and infrastructure that hold it all together. You see AI as a tool for solving real business problems, not as a hammer looking for a nail.
• You're energized by mission-driven work. You want your engineering career to matter beyond the code — and you see how better infrastructure for mental health care is better access to mental health care.
• You give direct, kind feedback. You've told someone a hard truth about their work and left the relationship stronger for it.

Bonus points for:

• Deeper machine learning fluency — hands-on experience with eval loops, model rollout, or production ML systems
• Healthcare, insurance, or claims experience
• Scaleup experience, Series B through D

Compensation and Benefits:

The expected base pay range for this position is $190,000 - $237,500, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About the Role

As a Senior Manager, HR Business Partner at Headway, you will serve as a strategic thought partner to our R+D executives. You’ll shape and execute people strategies that enable scale, strengthen leadership, and drive Olympic-level performance. Partnering closely with our leaders, you’ll provide counsel on organizational design, performance management, talent planning, and leadership development - balancing near-term priorities with long-term organizational health and cultural integrity. You’ll use data-driven insights and sound judgment to identify trends, influence decisions, and lead high-impact initiatives that elevate the employee experience, strengthen manager capability, and ensure our teams are empowered to perform at their best.

What You’ll Do

• Strategic Business Partnership: Act as a trusted advisor to executives. Anticipate organizational needs, connect people strategy to business outcomes, and challenge assumptions through evidence and insight.
• Talent Strategy & Performance: Lead performance management and talent review processes with rigor and fairness. Coach leaders to recognize and reward top performance, address underperformance, and build high-performing, inclusive teams.
• Organizational Design & Effectiveness: Partner with leaders to design scalable org structures, strengthen alignment, and enable growth. Use workforce analytics and org design principles to optimize spans, layers, and team health.
• Leadership Coaching & Influence: Build trusted relationships with executives and managers, providing candid, actionable feedback that sharpens leadership effectiveness. Reinforce Headway’s cultural principles and managerial excellence through coaching and systems.
• Analytical & Data-Driven Decision Making: Leverage people data to identify trends, diagnose root causes, and drive measurable improvements in organizational health.
• Project Management & Operational Excellence: Lead complex, cross-functional people initiatives end-to-end - from scoping and planning to flawless execution and follow-through. Balance strategic impact with hands-on execution to ensure scalability and continuous improvement.
• Cultural Stewardship & Employee Experience: Model and amplify Headway’s values and performance standards. Ensure fairness, inclusion, and consistency in decision-making. Surface patterns in sentiment and proactively strengthen engagement and trust.

You’d Be a Great Fit If You...

• Have 12+ years of progressive experience in HR or HR-adjacent roles (e.g., Chief of Staff, Strategy), with a track record of supporting senior executives in high-growth or scaling environments.
• Are a strategic operator who can anticipate organizational needs, shape people strategies, and influence through credibility and insight.
• Are data-driven, using qualitative and quantitative insights to inform decision-making, program design, and measurement of impact.
• Are a trusted coach and advisor, capable of balancing candor and empathy while influencing at all levels.
• Have deep expertise in org design, performance management, and leadership development.
• Thrive in fast-paced, high-growth settings where agility, sound judgment, and ownership are essential.
• Model Headway’s cultural principles and uphold our Olympic-level performance standard, driving clarity, accountability, and continuous improvement.

Compensation and Benefits:

The expected base pay range for this position is $180,000 - $250,000, based on a variety of factors including qualifications, experience, and geographic location. 

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

• Equity Compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About the Role

Headway is looking for a Senior Manager, People Systems & Operations to join the People team to lead our HR technology strategy and operations. You will work closely with the Director of Total Rewards and People Operations to build and optimize a scalable People technology ecosystem that supports Headway's growth. This is a unique opportunity to lead a team in managing our systems while enhancing the daily service experience for all Headway employees.

We're looking for a people leader with deep expertise in People Systems and Operations, including technical Workday administration skills, who is proactive and able to thrive in a high-growth environment. You will be critical to ensuring our People initiatives are supported by robust, high-performing systems that leverage emerging technologies and automation.

You Will

• Design strategic People Systems suite, including Workday optimizations in partnership with our People Systems' Engineer
• Improve technology in order to scale Headway's lifecycle operations to provide efficient support and automations for the employee lifecycle, as well as the internal People team
• Manage and develop a team of People systems and operations professionals, fostering a culture of continuous improvement and excellence
• Partner cross-functionally (IT, People Partners, etc) to visualize and plan system integrations and workflows intuitively and securely
• For all systems workflows and programs, whether creating new or optimizing legacy processes:
• Scope roadmaps and timelines focused on simplicity, efficiency, and the strategic adoption of AI tools
• Develop and lead Change Adoption programs, including the creation of training resources to ensure clarity for all staff
• Evaluate service delivery success, maintaining benchmarks for resolution and response times
• Continuously iterate and improve People team workflows
• Assess, recommend, and implement new tools and platforms as Headway grows

You'd Be a Great Fit If…

• You have 10+ years of experience in People Operations and Systems with at least 5 years specifically focused on Workday administration
• You have a track record of managing and developing a team of People professionals
• You are deeply knowledgeable and adept in Workday (HCM, Advanced Compensation, Absence & Time Tracking) and other People systems (examples: Google Workspace, CultureAmp, Greenhouse, Glean)
• You are a strategic thinker who can map out a multi-year roadmap while also executing tactical configurations and integrations
• You are highly organized and have a proven track record of managing highly complex, cross-functional projects with diverse stakeholders
• You function well in a high-paced environment, having experience managing workflows for thousands of employees and handling rapid scaling
• You're skilled in technical support and enablement, capable of training staff on new platforms and building internal knowledge centers
• You collaborate and build credibility across the organization through strong communication

Compensation and Benefits:

The expected base pay range for this position is $169,000-$212,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About the Role

This role sits at the intersection of patients, providers, and insurance, designing the billing and payment experiences that make Headway's financial engine feel simple, transparent, and trustworthy.

This is a complex, high-stakes design challenge. A single appointment at Headway touches insurance verification, claims processing, provider payouts, and patient billing — all with different timelines, edge cases, and failure modes. Today, confusion around billing is one of the top drivers of support tickets and a key factor in provider trust.

We’re building an AI first design team at Headway. Designers are expected to use AI tools like Claude, Cursor, and MagicPatterns to prototype and stay involved through launch and iteration directly in code. We’re looking for designers who’re already working this way and see AI as a primary part of their workflow. 

In This Role, You Will

• Own the end-to-end payment and billing experience across patients and providers. Navigate complexity with systems thinking. Payment flows touch insurance confirmation, claims, ERA ingestion, refunds, cancellation fees, and provider payouts. You'll map these dependencies and design experiences that absorb complexity rather than expose it.
• Start in planning mode, use tools like Claude.ai to clarify the problem space, understand data, and initial assumptions. 
• Prototype with Claude Code/Cursor and MagicPattern to build and iterate on the flows and IAs. Let AI generate the pixels and code while you define the right patterns, behaviors and quality. Partner with product & Eng to decide when to move into production. 
• Conduct research and directly talk to customers to validate the solution for most of BAU projects with the research team’s support.
• Contribute to the design system and culture, share your AI practice, prompts, and patterns with the design team.

Compensation and Benefits:

The expected base pay range for this position is $212,000 - $265,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About the Role

We are looking for our first Head of Communications to join Headway at a pivotal time for our company. In this role, you will lead a team responsible for defining, shaping and amplifying Headway’s story among a diverse set of audiences - patients, providers, payers, investors and employees -  establishing Headway as the trusted leader in the mental health category.  You will report to the Head of Brand, PMM & Communications and your team’s work will span corporate, product, consumer, financial and internal communications.  

As a masterful storyteller, you will be responsible for taking complex business initiatives and turning them into stories that are easy to understand, dynamic, memorable and influential in the market.  Given the nature of our industry, you’ll rely on your strong instincts and problem-solving skills to help us navigate highly regulated, sensitive dynamics. And as someone who loves the art & science of the job, you’ll leverage data, creativity and innovation to continue pushing the team forward, finding new ways to seize share of voice, drive key messages and foster positive sentiment in the market. 

You Will:

• Build our Communications Strategy:  Define our role & approach to communications at Headway, including the right channels and KPI’s that map back to our business objectives.  
• Craft Headway’s Most Important Stories: Demonstrating a deep understanding of our diverse audiences, business and industry dynamics, develop and steward core corporate, consumer, product, financial, and internal narratives that position us as a thought leader in mental health. Leverage data & AI to fuel an always-on machine of insights and creative storytelling.  In partnership with our executive team, help shape and amplify their voices as category experts.  
• Drive Share of Voice: Identify the channels, forums where our stakeholders are paying attention and then deliver outsized, positive attention for Headway in those channels
• Build & Protect Headway’s Reputation:  Working closely with cross-functional partners, anticipate and manage the communications implications of business and industry news. ​​Lead reputation and crisis planning, anticipating how issues may impact multiple sides of the marketplace and responding with clarity and care. 
• Turn Employees into Brand Advocates:  Ensure clear, consistent messaging that drives alignment, engagement, and trust across the organization during periods of growth and change.
• Attract & Retain a High-Performing Team:  Lead a team of communications professionals operating at the highest levels; consistently pushing them to grow and drive increasing impact in the org. 

You’d be a great fit if…

• You have 14+ years of experience and at least 7 years of management experience in communications, for healthcare, consumer or tech companies. 
• You’ve successfully led corporate, consumer and internal communications at high-growth, complex organizations that operate in highly-regulated environments.  
• Deep expertise in identifying, building & executing meaningful, enduring company narratives that result in positive reputation & trust for the organization. 
• You’re an excellent cross-functional collaborator; proven success translating your partner’s business challenges into communications strategies. 
• Strong customer-first instincts and the ability to influence without authority, especially during times of uncertainty. 
• Comfort operating in ambiguity in a fast paced environment with high visibility and impact
• You’re a force-multiplier, known for attracting and building high-performing teams and unlocking excellent work among all those around you. 

Compensation and Benefits:

The expected base pay range for this position is $251,200 - $314,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About The Role

As Headway works to build a new mental healthcare system that everyone can access, we’re facing unique operational challenges and opportunities that come with growing and scaling at an unparalleled rate. We’re pushing the boundaries of the existing healthcare system so that we can fulfill our promise to providers, patients, and payers to create access to high quality providers across the nation. In order to do that, we’re building a world class operations team that enables efficiency, growth, and quality, and as a member of this team, you will have the opportunity to have a material impact on the trajectory of Headway and help define a function core to the livelihood of our business and the impact we deliver for our partners and clients.

As a Clinical Operations Manager, you will lead high-impact, cross-functional initiatives that span teams and pods. You’ll operate as a thought partner to Clinical, Compliance, Legal, Data, and Operations leaders – helping shape objectives, influence priorities, and translate complex insights into actionable plans. In addition to owning critical operational workflows, you’ll design scalable systems, mentor team members, and drive initiatives that create durable, measurable impact across the organization. This role requires strong judgment, comfort with ambiguity, and the ability to drive alignment and execution across the organization.  

What you’ll do at Headway

• Design and build foundations for a variety of 0-1 and scaling initiatives within the Clinical Operations function designed to improve the quality and compliance of services provided at Headway.
• Collaborate cross-functionally to build, execute, monitor, and implement scalable products and processes that enable us to deliver on core business challenges.
• Assess and analyze data to develop and determine strategies for accelerating progress, proactively identify areas for improvement, and deliver on roadmap priorities and team OKRs.
• Build and manage a growing team to achieve these objectives.

You’ll be great for this role if you:

• 7+ years of experience in operational roles at high-growth companies, with some background in consulting, healthcare, business operations preferred but not required.
• 2+ years of people management experience; you are a team builder that is passionate about growing and developing talent
• Data is your first-language; you enjoy and are skilled at digging through complex data to solve ambiguous problems.
• You thrive in the unknown, and seek out opportunities to dive into unfamiliar challenges, drive towards outcomes, and shape strategy.
• You are operationally excellent, able to manage a large volume of moving pieces without breaking a sweat.
• You are a collaborator that proactively partners across teams while holding teams accountable for execution.
• You seek an environment that fosters individual growth through open-feedback and high-autonomy.
• You are motivated by the opportunity to make an impact on one of our generation’s defining problems: affordable mental healthcare

Compensation and Benefits:

The expected base pay range for this position is $110,400 - $172,500 based on a variety of factors including qualifications, experience, and geographic location. 

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

• Equity Compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

You Will

• Own Headway's SEM program end-to-end: campaign architecture, keyword strategy, bidding, budget allocation, and performance optimization across Google Ads and Microsoft Ads.
• Scale SEM spend efficiently: grow budgets toward $50M+ annually while maintaining target CAC and ROAS.
• Build incrementality measurement: design and run geo-lift studies, holdout tests, and brand/non-brand incrementality analysis.
• Optimize the full funnel: partner with Product and Engineering to improve post-click conversion from landing page through booked appointment.
• Partner directly with Engineering and Data Science: own tracking implementation, attribution infrastructure, and performance reporting.
• Leverage AI tools: Build and run AI agents in Claude Code that automate keyword expansion, ad copy generation, bid optimization signals, and competitive intelligence.

Who You Are

• 8+ years of SEM experience with deep hands-on expertise in Google Ads at scale.
• You have managed annual SEM budgets of $50M+. You know what it takes to scale spend while maintaining efficiency.
• You are a technical marketer. You work directly with Engineering and Data Science teams. You can write SQL and build dashboards.
• You measure what matters: incrementality testing, geo-lift studies, or MMM. You optimize for booked appointments, not vanity metrics.
• You own the full funnel: post-click optimization and conversion rate improvement with Product and Engineering.
• You actively manage AI agents as part of how you operate. Orchestrating AI is already part of your workflow.
• You want to own something. This is a single-IC role with a wide scope and real autonomy. 

Compensation and Benefits:

The expected base pay range for this position is $152,000 - $190,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About The Role

Headway's Care Partnerships team is building the behavioral health referral infrastructure for every health system in the US. Our BD team identifies, qualifies, and launches new health system partnerships — and we're scaling fast. As a BD Lead, Care Partnerships, you'll own the full BD motion for mid-market health system opportunities in your territory — from prospecting and cold outreach through qualification, pitching, and launch. You'll be the face of Headway to care management and clinical operations leaders, building relationships that turn into lasting referral partnerships. You'll also support our Associate Principals on larger enterprise deals and help mentor our growing BDR team.

You will: 

• Own and drive mid-market health system opportunities from first touch through launch
• Build relationships with Director+ care management, population health, and clinical operations leaders
• Run outbound and manage inbound leads across your assigned states
• Develop account strategies that consider long-term adoption, not just short-term wins
• Support Associate Principals with research, prep, and account coverage on enterprise opportunities
• Collaborate cross-functionally with Partner Success, Product, and Operations to ensure successful launches

You will love this role if:

• You have 5+ years of full-cycle BD or sales experience in healthcare, health tech, or a related industry
• You've sold into health systems, clinics, or provider organizations and understand care management workflows
• You are a strong relationship builder who can earn trust with Director+ leaders
• You can own a pipeline end-to-end — prospecting, qualifying, pitching, and closing
• You are strategic and scrappy — you think long-term about accounts but aren't afraid to pick up the phone
• You are a clear, concise communicator who can pitch Headway's value prop with credibility
• You seek an environment that fosters individual growth through open-feedback and high-autonomy
• You are motivated by the opportunity to face off against one of our generation’s defining problems: access to mental healthcare

Compensation and Benefits:

The expected base pay range for this position is $110-$160K, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About the Role

As Headway deepens its partnership with one of our most strategic national health plans, we're looking for an Associate Principal, Payer Partnerships to own the commercial relationships and channel strategy that will expand our footprint and make Headway the go-to mental health partner across the plan's book of business. Reporting to our Principal, Payer Partnerships, you'll work at the intersection of payer commercial teams, building the trust and advocacy that turn a strong partnership into a dominant one.

You will:

• Develop and strengthen senior-level relationships with commercial leadership at our health plan partner, ensuring Headway is known, trusted, and actively championed across their organization
• Develop Headway's understanding of patient acquisition channels, forming a point of view on which segments have appetite for deeper Headway engagement, which partners can facilitate that, and what the strategic tradeoffs are
• Collaborate with internal, cross functional stakeholders to deliver insights to inform product and operations strategy
• Drive strategic initiatives that deepen the partnership, identifying where Headway can expand its role, generate new demand, and increase stickiness across the plan's commercial ecosystem
• Build in a way that scales: document your approach so the commercial channel playbook you develop can be replicated across other accounts

You'd be a great fit if...

• You have a minimum of 7+ years of experience in the healthcare space, preferably in roles within Business Development, or in Strategic Partnerships/Customer-facing roles
• You have a track record of building meaningful relationships from scratch in complex, matrixed organizations — and you do it strategically, not just by being personable
• You've worked in or closely adjacent to the commercial side of healthcare, like at a digital health company with payer or employer channel exposure
• You don't wait for clarity to come to you; when the path forward is unclear, you identify the right questions, find the people and data that can answer them, and form a point of view before anyone asks you to
• You are operationally excellent, able to manage multiple high impact customers and large volume of moving pieces without breaking a sweat
• You think in playbooks. You don't just execute; you document your logic so others can build on it

Compensation and Benefits:

The expected base pay range for this position is $130,000-$200,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

Other compensation includes: discretionary bonuses and/or commission. Commission payments are monthly.

About The Role

At Headway, we're building the future of behavioral health quality and safety. We're hiring a Clinical Quality Lead to support our clinical quality monitoring initiatives and our Ongoing Professional Practice Evaluation Program for our network of therapists. You'll work cross-functionally with Operations, Compliance, Product, Engineering, and other teams to build robust clinical quality frameworks and optimize chart review workflows. This is an exceptional opportunity to reimagine how behavioral health quality is defined and measured at a rapidly scaling, mission-driven company.

You will:

• Support our Professional Practice Evaluation programs, directly improving clinical outcomes across our provider network of therapists
• Conduct routine chart reviews and monitoring, providing feedback to clinicians and creating remediation plans for documentation concerns
• Collaborate with Operations team to develop automated quality monitoring systems
• Work closely with clinical teams and peer reviewers, building clinical oversight capabilities as we scale
• Partner with cross-functional teams to optimize workflows and create scalable feedback systems for providers

You will love this role if:

• You are a clinician – have 5+ years of post-graduate experience as an Independently Licensed Therapist (LPC, LCSW,  PhD, or PsyD) 
• You have experience completing quality chart reviews and audits for healthcare organizations, with a track record of training others on clinical documentation standards
• You are curious about how AI is transforming clinical practice — you're excited to help evaluate, validate, and shape how new AI tools are deployed responsibly and how they improve care quality at scale.
• You thrive as a collaborator, building bridges between clinical strategy and product, operations, and business teams
• You are a strategic first-principles thinker who can decompose complex problems into clear strategies and actionable plans
• You are motivated by the opportunity to improve access to high-quality behavioral healthcare at scale

Compensation and Benefits:

The expected base pay range for this position is $105,400 - $155,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About Headway

Headway's mission is to build a new mental health care system that everyone can access. We've built technology that takes the hardest parts of mental healthcare — finding the right provider, navigating insurance, managing payments — and makes them simple. We're now one of the fastest-growing companies in healthcare, with more than 200,000 patients finding care through Headway and thousands of therapists using our platform to grow their practices.

About Patient Core Experience at Headway

The Patient Core Experience team owns how patients find the right therapist on Headway. From search through the first several sessions, our four engineering pods — Onboarding, Profiles + Checkout, Ranking + Relevance, and Activation — build the systems that make great therapeutic matches happen.

We operate a three-sided marketplace (patients, providers, payers) with real complexity and massive impact. We're evolving from a provider directory into an intelligent matching platform that uses communication style, data-backed expertise signals, and patient-reported outcomes to connect people with therapists who are genuinely right for them.

Principles that guide us:

• Matching quality is the foundation of therapeutic outcomes — we obsess over getting patients to the right provider
• We ship fast and learn fast, but we protect patient trust above all else
• We build for the whole marketplace: patients, providers, and payers
• ML powers our systems, but empathy drives our product

The Problems You'll Solve

This role exists because we have hard, specific challenges that need senior engineering leadership to crack. Here's what your first year looks like:

Build an ML-powered matching system from the ground up. Our current matching is largely filter-based. We need to move to ML-powered ranking that incorporates provider communication style, expertise signals, and patient outcome data — without degrading the patient experience during the transition. You'll define the technical strategy for how we get there and own the execution across multiple pods.

Rearchitect team topology as the product evolves. We have four pods today, but the boundaries between ranking, activation, and onboarding will shift as we move toward intelligent matching. You'll need to evolve team structure, ownership boundaries, and technical interfaces as the product changes shape. This includes scaling the org from ~18 to ~25+ engineers while maintaining velocity and quality.

Close the gap between engineering output and patient outcomes. We have patient funnel metrics (intake-to-match, match-to-book, book-to-retained) but engineering doesn't yet co-own them tightly enough with Product and Data. You'll establish the operating model where engineering, product, and data science jointly own these metrics in a true triad — not one where engineering is an execution arm.

Define how your teams build software in the AI era. This isn't about adding a bullet point on AI tooling. You'll set concrete standards for how your ~30 engineers use AI-assisted development — how it changes code review, testing strategy, onboarding, and potentially team composition. You'll also own the AI/ML strategy for the product itself: where we use ML models vs. heuristics, how we handle explainability in a healthcare context, and how we build patient trust in AI-driven recommendations.

Key Responsibilities

• Set engineering strategy for the core patient experience in partnership with Product and Data Science leadership
• Lead 3 Engineering Managers; scale the org from ~18 to ~30+ engineers over the next 18 months
• Co-own patient funnel metrics with your Product and Data counterparts — not just deliver against them
• Drive delivery of ML-powered ranking, reimagined patient onboarding, and patient activation systems
• Build an engineering culture with clear standards for velocity, quality, and technical excellence — starting with honest assessment of where we fall short today

What You Bring

Required experience:

• 10+ years of software engineering experience, 5+ years managing engineering managers
• Led engineering for a consumer or marketplace product where search, matching, ranking, or personalization was core to the business
• Scaled an engineering org through a high-growth phase (25+ to 50+) while maintaining velocity and quality
• Technically strong enough to make sound architecture calls on ranking/ML systems, marketplace infrastructure, and consumer-facing surfaces — you don't write code daily, but you can review a system design and spot the problems
• Experience shipping ML-powered product features (search ranking, recommendations, personalization) at consumer scale
• Track record of moving business metrics (conversion, retention, engagement) through engineering-product partnership, not just delivering features on time
• Comfort working in a regulated industry where you can't just ship fast — you need to reason about bias, explainability, and patient safety in ML systems
• Practiced perspective on AI-augmented engineering workflows — you've led teams through adoption of AI development tools and have opinions on what changes and what doesn't

Nice-to-have:

• Healthcare experience or other regulated industries where data sensitivity and clinical consequences raise the stakes
• Experience with marketplace dynamics (supply/demand balancing, multi-sided incentive design)
• Experience building LLM-based product features (conversational interfaces, intelligent triage, AI-assisted workflows)
• Experience rethinking team structure or hiring profiles in response to AI productivity gains

Our Stack

Our platform runs on Python (Django/FastAPI) and TypeScript/React on the frontend. Elasticsearch powers search and ranking. PostgreSQL and Redis handle data storage and caching. We use dbt and Snowflake for data pipelines, Temporal for workflow orchestration, and custom ML models for matching. Everything runs on AWS.

You won't be writing code daily, but you'll need to engage deeply enough with these systems to make sound technical and organizational decisions.

You'll Love This Role If You Want To

• Solve a genuinely hard problem at the intersection of ML, marketplace dynamics, and healthcare — where getting matching right has real clinical consequences
• Shape an engineering org during a foundational transition, with high autonomy and strong executive support
• Co-own patient outcomes, not just engineering output
• Work at a company where the mission isn't marketing copy — patients are actually getting access to therapy they couldn't get before

Compensation and Benefits:

The expected base pay range for this position is $264,000 to $330,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About The Role

At Headway, we're building the future of behavioral health quality and safety. We're hiring a Principal for Clinical Quality to spearhead our clinical quality monitoring initiatives and lead our Ongoing Professional Practice Evaluation Program for our network of NPs and MDs/DOs. You'll work cross-functionally with Operations, Compliance, Product, Engineering, and other teams to build robust clinical quality frameworks and optimize chart review workflows. This is an exceptional opportunity to reimagine how behavioral health quality is defined and measured at a rapidly scaling, mission-driven company.

You will:

• Lead Headway's clinical quality strategy, developing protocols and processes that uphold safety, efficiency, and effectiveness standards for the practice.
• Build and scale our Professional Practice Evaluation programs, directly improving clinical outcomes across our provider network of NPs and MDs/DOs
• Conduct routine chart reviews and monitoring, providing feedback to clinicians and creating remediation plans for documentation concerns
• Collaborate with Operations team to develop automated quality monitoring systems
• Supervise clinical teams and peer reviewers, building clinical oversight capabilities as we scale
• Partner with cross-functional teams to optimize workflows and create scalable feedback systems for providers

You will love this role if:

• You are a licensed Psychiatric Mental-Health Nurse Practitioner (PMHNP) with 6+ years of post-graduate experience in both clinical practice and fast-paced business environments
• You have extensive experience completing quality chart reviews and audits for healthcare organizations, with a track record of training others on clinical documentation standards
• You are a thought leader passionate about reimagining behavioral health quality, ideally with experience across traditional healthcare organizations, public health systems, and/or healthcare startups
• You thrive as a collaborator, building bridges between clinical strategy and product, operations, and business teams
• You are a strategic first-principles thinker who can decompose complex problems into clear strategies and actionable plans
• You have experience supervising clinicians or large provider teams, with strong performance management skills
• You are motivated by the opportunity to improve access to high-quality behavioral healthcare at scale

Compensation and Benefits:

The expected base pay range for this position is $169,600 - $265,000, based on a variety of factors including qualifications, experience, and geographic location. 

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

• Equity Compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About The Role

At Headway, we're building the future of behavioral health quality and safety. We're hiring an Associate Medical Director for Clinical Quality to spearhead our clinical quality monitoring initiatives and lead our Ongoing Professional Practice Evaluation Program for our network of NPs and MDs/DOs. You'll work cross-functionally with Operations, Compliance, Product, Engineering, and other teams to build robust clinical quality frameworks and optimize chart review workflows and ensure patient safety. This is an exceptional opportunity to reimagine how behavioral health quality is defined and measured at a rapidly scaling, mission-driven company.

You will:

• Lead Headway's clinical quality strategy, developing protocols and processes that uphold safety, efficiency, and effectiveness standards for the practice.
• Build and scale our Professional Practice Evaluation programs, directly improving clinical outcomes across our provider network of NPs and MDs/DOs
• Conduct routine chart reviews and monitoring, providing feedback to clinicians and creating remediation plans for documentation concerns
• Collaborate with Operations team to develop automated quality monitoring systems
• Lead response to acute patient safety issues
• Supervise clinical teams and peer reviewers, building clinical oversight capabilities as we scale
• Partner with cross-functional teams to optimize workflows and create scalable feedback systems for providers

You will love this role if:

• You are a licensed psychiatrist (MD/DO) with 3+ years of post-graduate experience in both clinical practice and fast-paced business environments
• You have extensive experience completing quality chart reviews and audits for healthcare organizations, with a track record of training others on clinical documentation standards
• You are a thought leader passionate about reimagining behavioral health quality, ideally with experience across traditional healthcare organizations, public health systems, and/or healthcare startups
• You thrive as a collaborator, building bridges between clinical strategy and product, operations, and business teams
• You are a strategic first-principles thinker who can decompose complex problems into clear strategies and actionable plans
• You have experience supervising clinicians or large provider teams, with strong performance management skills
• You are motivated by the opportunity to improve access to high-quality behavioral healthcare at scale

Compensation and Benefits:

The expected base pay range for this position is $179,200 - $280,000, based on a variety of factors including qualifications, experience, and geographic location. 

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

• Equity Compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About The Role

Headway is scaling our care partnerships across the US and we’re hiring a Senior Partner Success Associate, Care Partnerships, to both support the growing number of partners that entrust Headway with connecting their patients with our high quality, behavioral health network. 

You’ll work cross functionally with internal teams (Strategy, Product, Operations) to ensure our care partners remain excited to work with Headway, while also deepening external health system, medical clinic, and strategic partner relationships to identify avenues for deeper partnership. This is an exceptional opportunity to own high-impact objectives at a rapidly scaling, mission driven company. 

You will: 

• Be responsible for the happiness of our care partners and clinicians
• Create new strategies to engage with clinicians that refer to Headway
• Support the team in preparing for executive meetings with partners
• Build and grow relationships with care partners’ (health systems, medical clinics, and other strategic partners) teams and leadership 
• Leverage data to generate insights and identify new opportunities for partnership growth 
• Collaborate with cross functional, internal stakeholders to deliver insights to inform product and operations strategy

You will love this role if:

• You have a minimum of 3+ years of experience in the healthcare space, preferably in roles within Customer Success, or in Strategic Customer-facing roles
• You bring deep exposure to health system or provider group models and economics
• You are a relationship builder, and delight in forging meaningful bonds across all levels of an organization
• You thrive in ambiguity, and seek out opportunities to dive into unfamiliar challenges, drive towards outcomes, and shape strategy
• You are operationally excellent, able to manage multiple high impact customers and large volume of moving pieces without breaking a sweat
• You seek an environment that fosters individual growth through open-feedback and high-autonomy
• You are motivated by the opportunity to face off against one of our generation’s defining problems: access to mental healthcare

Compensation and Benefits:

The expected base pay range for this position is $85,000-$124,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

The Work

Fullstack at Headway means end-to-end ownership. You’re building reliable abstraction layers over a fragmented healthcare system and translating them into seamless, empathetic user experiences. What you could work on:

• Therapist Practice Management: Build a best-in-class platform for Headway therapists to run their businesses. You'll own features from the database schema to the UI, creating intuitive web experiences for scheduling, clinical notes, and payment management.
• Patient-First Experiences: We’re moving toward a patient-centric model. Transform the therapist search experience by building the frontend interfaces and backend APIs that power personalized care recommendations, longitudinal data views, and seamless patient-provider matching.
• The Modern AI-enabled Clinical System: Help design and build the interfaces and systems that manage clinical data. Build high-integrity experiences for treatment plans and progress notes, integrating AI-powered clinical intelligence to give providers their time back.
• Frictionless Onboarding: Turn the historically nightmare process of insurance credentialing into a sleek, consumer-grade web experience. Build products and tooling to get providers in-network and scaling their practice in record time.

Our Stack

• Languages: TypeScript, Python 3
• Frontend: React, Remix, Next.js
• Backend & Storage: FastAPI, SQLAlchemy, Postgres, Redis, Snowflake
• Infrastructure: AWS, Temporal, Kafka
• Ops: Datadog, Sentry, PagerDuty
• AI Tools: Cursor, Claude, Gemini, Eddy (our in-house cloud agent harness)

Who You Are

• End-to-End Product Builder: You care just as much about the API architecture as you do the user experience. You seamlessly context-switch between backend logic and frontend state management.
• Owns Outcomes, Not Tasks: You've been handed ambiguous problems and turned them into shipped software. You know how to define the solution, pull in the right people across teams, and keep things moving when priorities shift.
• Sets the Technical Standard: You make technical decisions that optimize for maintainability and scale, not just shipping speed. You proactively improve your team's engineering velocity - whether that's refining tooling, improving automation, or establishing patterns that prevent entire categories of bugs.
• Mentor by Default: You pull engineers into design discussions without being asked. Your code reviews teach, not just gatekeep. You make sure knowledge gets shared across the team, not siloed in one person's head.
• Ships Fast, Iterates Faster: You can move from problem statement to working solution quickly. You'd rather ship a good v1 this week than a perfect v1 next month. Real feedback from therapists and patients is worth more than another round of design review.
• Quick Study in Complex Domains: Healthcare is a maze of payers, regulations, and exceptions. You don't need prior healthcare experience, but you need to be someone who dives into unfamiliar domains and builds a working mental model fast.
• Motivated by Impact: You want your engineering skills applied to problems that matter. Mental healthcare access is broken in America, and you want to be part of fixing it.
• Communicates with Precision: Whether it's a Slack thread, a design doc, or a cross-team meeting, you communicate clearly and concisely. You know that great engineering is wasted if you can't bring people along.
• AI Frontier Tinkerer: You don't just use AI tools - you push their limits. You've experimented with applying LLMs to real workflows, whether that's code generation, operational automation, or developer tooling. You bring a builder's mindset: what can we automate, what should stay human, and how do we ship it responsibly in healthcare?

Our Interview Process

After you apply to Headway, here are some details of what to expect during the interview process.

• Initial screen: You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background. 
• First round: You'll do a live coding interview with Karat, our technical interviewing partner. It's a great opportunity to showcase your problem-solving skills and learn more about what our engineering team is building.
• Final rounds: You’ll meet several team members for technical and non-technical interviews and leave with a fuller picture of what it’s like to work at Headway.
• References and the Offer: Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!

Compensation & Benefits

• Salary: $168,300 - $237,500 base salary plus a competitive equity package.
• Comprehensive Benefits: Medical, dental, vision, HSA/FSA, 401(k), Carrot Fertility reimbursement, and 16-week parental leave.
• The Mission: We reimburse your therapy and provide a professional development budget. We believe in what we’re building.
• Time Off: 13 holidays, a full week off in December, and flexible PTO.

The Work

Backend at Headway involves high-stakes logic. You’re building a reliable abstraction layer over a fragmented healthcare system. What you could work on:

• The Modern AI-enabled Clinical System: Help design and build the systems that store and manage clinical data. This isn't just a database; it's a high-integrity system for treatment plans, progress notes, patient history, and AI-powered clinical intelligence - from session transcript-to-note generation to automated summaries that give providers their time back.
• The Insurance Billing Engine: We apply AI pragmatically (blog) to reduce administrative burdens for providers and handle the burden of traditional billing workflows. You’ll scale the systems that handle the unique, often nonsensical rules of every major insurance payer to accurately estimate and file claims hundreds of thousands of times per month. 
• Patient-First Infrastructure: We’re moving toward a patient-centric model. Build the backend services that power personalized care recommendations, health tracking, and longitudinal data views as well as innovative user experiences to help patients find a therapist that meets their needs
• Financial Integrity: Work on the ledger systems that ensure 70,000+ providers get paid accurately. This requires building for idempotency and strict consistency in a multi-party marketplace.

Our Stack

• Languages: Python, TypeScript
• Storage: Postgres, Redis, Snowflake
• Infrastructure: AWS, Temporal
• Ops: Datadog, Sentry, PagerDuty
• AI Tools: Cursor, Claude, Gemini, Eddy (our in-house cloud agent harness)

Who You Are

• Owns Outcomes, Not Tasks: You've been handed ambiguous problems and turned them into shipped software. You know how to define the solution, pull in the right people across teams, and keep things moving when priorities shift.
• Sets the Technical Standard: You make technical decisions that optimize for maintainability and scale, not just shipping speed. You proactively improve your team's engineering velocity - whether that's refining tooling, improving automation, or establishing patterns that prevent entire categories of bugs.
• Mentor by Default: You pull engineers into design discussions without being asked. Your code reviews teach, not just gatekeep. You make sure knowledge gets shared across the team, not siloed in one person's head.
• Ships Fast, Iterates Faster: You can move from problem statement to working solution quickly. You'd rather ship a good v1 this week than a perfect v1 next month. Real feedback from therapists and patients is worth more than another round of design review.
• Quick Study in Complex Domains: Healthcare is a maze of payers, regulations, and exceptions. You don't need prior healthcare experience, but you need to be someone who dives into unfamiliar domains and builds a working mental model fast.
• Motivated by Impact: You want your engineering skills applied to problems that matter. Mental healthcare access is broken in America, and you want to be part of fixing it.
• Communicates with Precision: Whether it's a Slack thread, a design doc, or a cross-team meeting, you communicate clearly and concisely. You know that great engineering is wasted if you can't bring people along.
• AI Frontier Tinkerer: You don't just use AI tools - you push their limits. You've experimented with applying LLMs to real workflows, whether that's code generation, operational automation, or developer tooling. You bring a builder's mindset: what can we automate, what should stay human, and how do we ship it responsibly in healthcare?

Our interview process

After you apply to Headway, here are some details of what to expect during the interview process.

• Initial screen: You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background. 
• First round: You'll meet with an engineer on the team to do some live coding and learn more about the engineering team.
• Final rounds: You’ll meet several more team members for technical and non-technical interviews and leave with a fuller picture of what it’s like to work at Headway.
• References and the Offer: Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!

Compensation & Benefits

• Salary: $168,300 - $237,500 base salary plus a competitive equity package.
• Comprehensive Benefits: Medical, dental, vision, HSA/FSA, 401(k), Carrot Fertility reimbursement, and 16-week parental leave.
• The Mission: We reimburse your therapy and provide a professional development budget. We believe in what we’re building.
• Time Off: 13 holidays, a full week off in December, and flexible PTO.

#LI-BM1

About the Role

Group practices are one of Headway's biggest growth levers — and one of its most complex design challenges. Unlike solo providers, group practices operate through owners, admins, supervisors, and supervisees, each with different permissions, workflows, and goals. A single group practice might onboard dozens of providers simultaneously, manage supervisory billing relationships across multiple states, and need practice-level reporting that doesn't exist today.

This is also a massive business opportunity. Supervisory billing — enabling provisionally licensed therapists to bill insurance through Headway — represents a ~250K new provider TAM and over $100M in annual revenue potential. It's the #2 reason we lose group practice sales (after rates), and we're just getting started: we launched in-product onboarding in Q1 and are expanding state-by-state throughout 2026.

As a Staff Product Designer for Group Practices, you'll be the design anchor for the only segment-based pod at Headway. You won't just own a surface — you'll own a customer. That means designing across the full lifecycle: from how group practices discover and join Headway, to how they onboard and activate supervisees, to how they manage packaging tiers and track practice performance. You'll think like a business builder — understanding the revenue model, making sharp prioritization calls, and designing product experiences that directly drive growth.

We're building an AI-first design team at Headway. Designers are expected to use AI tools like Claude, Cursor, and MagicPatterns to prototype and stay involved through launch and iteration directly in code. We're looking for designers who are already working this way and see AI as a primary part of their workflow.

In this role, you will:

• Own the design of the group practice experience end-to-end — from onboarding and supervisory billing, to packaging and SLA compliance, to practice management and admin tooling. You're the design anchor for the entire segment.
• Drive supervisory billing from early product to nationwide scale — design the onboarding, activation, and in-product experience for supervisors and supervisees as we expand from NY to all 50 states.
• Design for admins and owners as your primary persona — build bulk workflows, role-based views, multi-provider management, and practice-level analytics that solo-focused products don't support.
• Adapt platform-wide launches for group practices — when Headway ships packaging, identity verification, or onboarding improvements, you'll ensure they work for the group practice context, often requiring fundamentally different design approaches.
• Start in planning mode, using tools like Claude.ai to clarify the problem space, understand data, and test initial assumptions. Prototype with Claude Code/Cursor and MagicPatterns to build and iterate on flows and IAs. Let AI generate the pixels and code while you define the right patterns, behaviors, and quality. Partner with product & Eng to decide when to move into production.
• Partner closely with Sales and Customer Success, who have deep relationships with group practice customers — translate their insights into product direction and design decisions.
• Contribute to the design system and culture, share your AI practice, prompts, and patterns with the design team.

You'll be a great fit if you:

• Have 8+ years of product design experience, with significant time spent designing for multi-user systems with different roles and permissions (admins, operators, end users)
• Have 0→1 product experience — you've designed new product lines, validated business models through design, or taken a product area from early concept to scale
• Think like a business builder — you understand revenue models, can connect design decisions to business outcomes, and make sharp prioritization calls about where design effort creates the most value
• Have designed for platforms or marketplaces where segment-specific needs must be balanced with platform consistency — you know when to customize and when to unify
• Bring strong visual and interaction design craft across both growth surfaces (onboarding, activation) and product surfaces (dashboards, tooling, operational workflows)
• Are comfortable partnering with Sales and CS as key stakeholders — not just PM and Eng — and translating customer relationships into product insights
• Are comfortable with AI prototyping tools (Claude Code, Cursor, MagicPatterns) and see them as a core part of how you work
• Want your work to make a meaningful difference in people's lives — by helping group practices thrive on Headway, you're expanding access to affordable mental healthcare at scale

Compensation and Benefits:

The expected base pay range for this position is $212,000 - $265,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

As a Strategic Finance Lead, GTM, you will sit within the Strategic Finance team and play a critical role in ensuring capital is deployed efficiently across Provider and Patient Growth initiatives. This is a highly cross-functional role for someone who thrives at the intersection of financial analysis and strategic decision-making. You'll build models, track performance, and surface insights that guide how we allocate resources and scale our GTM investments.

You Will

• Build and maintain financial models to assess GTM investment efficiency, scenario plan, and evaluate trade-offs across growth initiatives
• Own budgeting and forecasting processes for GTM spend, partnering with budget owners to align plans with strategic priorities.
• Analyze operating KPIs and funnel data to evaluate unit economics, channel performance, and overall GTM effectiveness
• Partner cross-functionally to surface insights and support strategic decision-making
• Develop dashboards, reporting, and executive-ready materials to communicate progress against goals

You’d be a great fit if…

• You have 4+ years of professional experience, ideally in a mix of financial services (Consulting / Equity Research / Private Equity) and highly analytical roles at a fast-growing company (Strategic Finance)
• You are highly proficient in Google Sheets (advanced formulas) and Looker (or similar BI tools) and comfortable working with large datasets
• You are detail-oriented and have a “measure twice, cut once” approach when working with financial data
• You’re excited to work cross functionally with the business teams to develop a greater understanding of function-specific efficiency metrics and help course-correct where necessary
• You take ownership and are a resourceful self-starter—you proactively seek context, solve ambiguous problems, and anticipate stakeholder needs
• You are excited about AI and how it's reshaping finance, and you actively explore and apply AI tools to drive faster insights, greater efficiency, and smarter decision-making
• You communicate complex insights clearly, tailoring your message for different audiences (finance vs. marketing)
• You thrive in a fast-paced, cross-functional environment and enjoy collaborating with marketing, finance, and growth teams
• You are excited about joining a mission-driven company and driving marketing efficiency to improve mental healthcare access

Compensation and Benefits:

The expected base pay range for this position is $131,750 - $165,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

#LI-LN1

As Medical/Clinical Director, Payer Partnerships you will support Headway’s health plan relationships and payer strategy to continue expanding Headway’s provider network impact. You’ll work cross-functionally with teams across Headway, including Payer, Product, Growth, Marketing, Data & Analytics, and others.

As the only tech-enabled behavioral health Managed Services Organization (MSO) built with entirely in-house software, Headway has an unprecedented opportunity in the clinical space. Today, we support more than 60k Clinicians and hundreds of thousands of patients. Building a best in class digital product will impact clinicians and patients nationwide. Please note the internal title of this role may be subject to change.

You’ll be great for this role if:

• You are a Psychiatrist (MD/DO) or Clinical Psychologist (PhD) with 5+ years of experience as a clinician operating in a fast-paced, high growth business.
• You bring 2+ years of experience working in payer or partnership roles, ideally in technology environments.
• You are an industry influencer –  with demonstrated passion for reimagining how behavioral health is delivered and measured. This likely means you’ve worked in health plans, health systems, and / or healthcare startups. You speak at industry conferences.
• You are a proven thought leader with peer-reviewed publications, mainstream media articles, and/or other expert content. 
• You’re effective at communicating clinical information to non-clinical staff and can distill complex clinical processes and language in order to move product implementation forward. You have worked in a position that required communication with large populations, including leading presentations. Storytelling is one of your superpowers. 
• You have strong analytical skills and are experienced in analyzing and synthesizing data & research insights to inform strategy, drive innovation, and clearly demonstrate scientific and organizational value to customers.
• You are a creative thinker who loves white space and can explore data in new and different ways, expanding the way the field thinks about common problems.
• You are familiar with clinical quality measurement and peer review systems in healthcare.
• You are a collaborator – eager and adept at working in concert with product, operations, and sales teams to infuse clinical strategy across the org.
• You have general familiarity with healthcare regulations and laws surrounding corporate practice of medicine.
• You have past experience with a healthcare tech company and/or startup.
• You are based on or near the East Coast and are willing to travel.

You Will:

• Support Headway health plan partnerships and strategy
• Promote external relations with Payers through relationship building, presentations/reporting, sales meetings, and conference participation
• Develop a critical understanding of how mental health clinicians utilize digital tools to deliver high quality care and document in a compliant manner
• Work collaboratively with cross functional teams including product, design, growth, marketing, payer relations, data & analytics, and operations
• Be willing to travel. 

Compensation and Benefits:

The expected base pay range for this position is $211,200 - $330,000, based on a variety of factors including qualifications, experience, and geographic location. 

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

• Equity Compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

As a Senior Revenue Accountant, you will play a key role in ensuring accurate and compliant revenue accounting for a fast-growing company. You’ll focus on ASC 606 revenue recognition, month-end close, reporting, and building scalable processes and systems. This role is highly cross-functional, partnering with Finance, Legal, Data, Product, and Engineering teams to ensure revenue is reported accurately and efficiently. This role offers an opportunity to apply creative thinking and strong problem-solving skills to make a lasting impact on Headway’s growth and operations.

You will:

• Support revenue month-end close activities, including preparing journal entries, reconciliations, and account analyses to deliver timely and accurate results
• Contribute to the design, implementation, and documentation of scalable revenue processes, policies and controls to support growth
• Partner with Engineering, Product, Ops and Data teams to develop and test billing and revenue systems
• Analyze large data sets to validate underlying system configurations and financial reporting outputs
• Support annual audit requests and provide documentation for revenue-related testing
• Identify and implement process improvements, leveraging AI tools and automation to drive efficiency in revenue accounting operations
• Lead revenue-related projects, coordinating cross-functional partners, tracking progress, and delivering measurable business impact

You’ll be great for this role if:

• You have 3+ years of accounting and/or audit experience
• You have a Bachelor’s degree in Accounting or another relevant field
• You are a CPA (or CPA track)
• You have strong working knowledge of ASC 606 (a plus, but not required)
• You have a Big 4 audit background and/or experience in high-growth environments
• You have strong communication skills and the ability to collaborate effectively across teams
• You are a problem solver and can work efficiently under pressure
• You take initiative and enjoy tackling complex accounting and business challenges

Compensation and Benefits:

The expected base pay range for this position is $95,200- $140,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About the Role

Every provider who joins Headway starts with onboarding — a multi-step credentialing process that collects licenses, CAQH data, NPI verification, payer enrollment, and more. Today, only ~20% of qualified providers make it from interest to their first appointment. That gap represents over $100M in unrealized annual revenue and, more importantly, tens of thousands of patients who can't access the care they need.

We're not looking to optimize the existing form. We're looking to replace it. This role will lead the design of an AI-agent-powered onboarding experience that fundamentally reimagines how providers join Headway — transforming a high-friction, multi-page credentialing flow into an intelligent, conversational experience that gets providers credentialed and seeing patients faster than they thought possible.

We're building an AI-first design team at Headway. Designers are expected to use AI tools like Claude, Cursor, and MagicPatterns to prototype and stay involved through launch and iteration directly in code. We're looking for designers who are already working this way and see AI as a primary part of their workflow.

In this role, you will:

• Own the end-to-end provider onboarding experience from lead form submission through credentialing to first appointment. You'll be the design anchor for the Onboarding pod, partnering with PM and Eng to drive the biggest conversion lever in our provider funnel.
• Design AI-agent-powered intake flows that replace manual, multi-page credentialing forms with intelligent interactions. You'll define what agentic onboarding looks like at Headway — new interaction patterns, trust signals, and automation boundaries that don't yet exist in our design system.
• Scale our self-serve onboarding vision beyond v2. We've proven that product-led onboarding can dramatically improve conversion; you'll push this further, enabling providers to go from interest to credentialed with minimal human intervention.
• Start in planning mode, using tools like Claude.ai to clarify the problem space, understand data, and test initial assumptions. Prototype with Claude Code/Cursor and MagicPatterns to build and iterate on flows and IAs. Let AI generate the pixels and code while you define the right patterns, behaviors, and quality. Partner with product & Eng to decide when to move into production.
• Conduct research and talk directly to providers to validate solutions, with the research team's support. Understand why providers get stuck, what builds their confidence, and where automation helps vs. hinders.
• Contribute to the design system and culture, share your AI practice, prompts, and patterns with the design team.

You'll be a great fit if you:

• Have 8+ years of product design experience, with significant time spent on onboarding, activation, or conversion-focused product work
• Have shipped measurable conversion improvements — you think in funnels, know how to diagnose drop-off, and get excited when a design change moves a metric
• Are a systems thinker who can reason about how a form redesign connects to CAQH, NPI, payer credentialing, and downstream provider activation — you design with awareness of the full pipeline
• Have experience designing agentic or AI-powered workflows — conversational flows, intelligent automation, or replacing manual processes with AI-driven experiences (not just chatbots)
• Bring strong visual and interaction design craft — you care deeply about the details and can produce polished, high-quality work at speed
• Are comfortable with AI prototyping tools (Claude Code, Cursor, MagicPatterns) and see them as a core part of how you work
• Want your work to make a meaningful difference in people's lives — this role directly impacts how many providers join Headway and how many patients get access to affordable mental healthcare

Compensation & Benefits:

The expected base pay range for this position is $212,000 - $265,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

As Headway’s Director of FP&A, you will build and manage a high-performing team overseeing corporate finance activities, operationalize KPIs to provide insight into business performance and develop best practices to ensure timely visibility into company performance. You will partner with cross-functional teams to understand performance, identify areas of opportunity, and support strategic decision-making. You will be a key player in driving coordination of strategic and financial planning processes as we scale. You will also serve as a trusted advisor and critical business partner to G&A functional leaders across the organization. This is an exciting opportunity for an experienced, detail-oriented leader who wants to make a significant impact on Headway’s growth and success.

You will: 

• Establish and drive financial planning processes, ensuring resource allocation stays within budget and forecasts are tightly linked to the company’s strategic goals
• Oversee the company-wide operating model, ensuring key inputs are linked to company growth and profitability for use in annual planning/budgeting and monthly forecasting
• Perform robust financial analysis on financial results and operating KPIs, identifying underlying trends and areas of opportunity
• Design and deliver monthly/quarterly reporting packages that tell the story behind the numbers for the exec team and Board
• Optimize systems to ensure automation of critical processes as we scale
• Support competitive intelligence, M&A and other corporate development initiatives
• Hire and develop a high-performing FP&A team to support the needs of the business
• Drive capital allocation strategy, cash management, and expense governance
• Support investor reporting, due diligence, and board-level discussions

You’d be a great fit if:

• You have 10-15+ years of strategic finance/FP&A experience at a high-growth startup, ideally including 2+ years of consulting/banking/investing
• You understand that people drive change, not spreadsheets, and are passionate about working with partners across all levels of the organization to steer progress
• You have exceptional analytical skills with the ability to drill down into the weeds while maintaining a strategic lens
• You are excited about AI and how it's reshaping finance, and you actively explore and apply AI tools to drive faster insights, greater efficiency, and smarter decision-making
• You have strong financial acumen and expertise in building financial models to support multiple business needs
• You are a curious self-starter, resourceful and have a knack for problem-solving
• You are a natural leader who enjoys hiring, mentoring and managing people to reach their highest potential 
• You’re energized by joining an early-stage startup and making immediate impact in a high-growth environment 
• You are an excellent communicator with strong interpersonal skills

Compensation and Benefits:

The expected base pay range for this position is $169,600 - $265,000, based on a variety of factors including qualifications, experience, and geographic location.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

• Equity Compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

#LI-LN1

As Senior Data Science Manager for Customer Experience, you will define and lead the insights strategy for Headway’s customer experience ecosystem. The team’s mission is to deliver timely, meaningful support when it matters most through best-in-class tooling, automation, and AI.

You will report into Headway’s Platform Group, a mission-critical pillar that ensures the systems behind our insurance platform reliably power patient, provider, and payer experiences. World-class support is a core part of customer experience and essential to Headway’s growth. 

You will partner closely with Product, Engineering, and Customer Experience to deeply understand and improve the customer support experience. You will define the right questions, proactively uncover opportunities, and use data to guide decisions from early concept through launch and iteration. You will set the standards for how we define support quality and effectiveness, ensuring your team delivers work that leads to real, measurable improvements.

You will:

• Lead and grow a high-performing team of Data Scientists, fostering a culture of technical excellence and strategic thinking. 
• Develop quarterly roadmaps with cross-functional partners, align Data Science resources, and oversee execution of timely and high-quality work.
• Drive insights and decisions through strategic analysis, reporting, predictive modeling, and experimentation.
• Architect a measurement framework that isolates how human agents, AI, and company policies contribute to customer sentiment to determine which levers we can pull to improve satisfaction. 
• Partner cross-functionally to design and build performance management systems to ensure world-class customer experience at scale.
• Stay close to the data by tackling strategic projects yourself, surfacing gaps in our data and understanding of our customers. 
• Translate complex technical findings into clear, actionable recommendations for executive stakeholders.

You will love this role if:

• You have 8+ years of experience in data science or analytics roles
• You have 3+ years of experience managing and developing teams
• You have experience working on customer experience, support systems, or service operations (highly preferred)
• You have proven success partnering cross-functionally with Product, Engineering, and Customer Experience
• You have deep expertise in measurement science and causal inference, especially Bayesian A/B testing, with the ability to coach others through complex experimental design
• You are proficient in forecasting and predictive modeling techniques
• You have hands-on technical fluency in SQL and Python or R
• You have experience adopting and championing AI-assisted tools to accelerate and automate data workflows
• You have strong communication and stakeholder management skills

Why This Role is Exciting

• You'll shape analytics for the Customer Experience at Headway, informing the vision and roadmap for improving support operations and product at scale.
• You'll play a key role in how automation and AI reduce friction and improve support experiences
• You'll partner closely with senior leadership and directly influence company strategy and growth

Compensation and Benefits:

The expected base pay range for this position is $212,000 - $265,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

As Headway’s Senior Manager, FP&A, you will be at the center of the financial processes that drive operational excellence and keep our business moving forward while holding accountability. You will support the overall corporate finance function through the cadence of monthly reporting, forecasting and exec-level KPI reviews. You will serve as a critical business partner to G&A functional leaders across the organization, and identify areas of opportunity while supporting strategic decision-making. This is an exciting opportunity for an experienced, detail-oriented leader who wants to make a significant impact on Headway’s growth and success.

You will: 

• Drive financial planning processes, ensuring the company resource allocation stays within budget and forecasts are tightly linked to the company’s strategic goals
• Support and evolve the company-wide operating model, ensuring key inputs are linked to company growth and profitability and the model is a reliable foundation for forecasting and planning
• Perform robust financial analysis on financial results and operating KPIs, identifying underlying trends and areas of opportunity
• Build and deliver monthly/quarterly reporting packages that tell the story behind the numbers for the exec team and Board
• Leverage tooling/systems to ensure automation of critical processes as we scale
• Support competitive intelligence, M&A and other corporate development initiatives
• Support investor reporting, due diligence, and board-level discussions

You’d be a great fit if:

• You have 8-10+ years of strategic finance/FP&A experience at a high-growth startup, ideally including 2+ years of consulting/banking/investing
• You understand that people drive change, not spreadsheets, and are passionate about working with partners across all levels of the organization to steer progress
• You have exceptional analytical skills with the ability to drill down into the weeds while maintaining a strategic lens
• You have strong financial acumen and expertise in building financial models to support multiple business needs
• You are excited about AI and how it's reshaping finance, and you actively explore and apply AI tools to drive faster insights, greater efficiency, and smarter decision-making
• You are a curious self-starter, resourceful and have a knack for problem-solving
• You’re energized by joining an early-stage startup and making immediate impact in a high-growth environment 
• You are an excellent communicator with strong interpersonal skills

Compensation and Benefits:

The expected base pay range for this position is $144,000 - $225,000 based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

#LI-LN1

About the role:
Headway is seeking an AP Manager to own the accounts payable function and build scalable, efficient processes that support accurate financial reporting and audit readiness. In this role, you’ll manage AP operations, month-end close, reconciliations, and audit support while partnering cross-functionally to optimize workflows and vendor management. This is a great opportunity for a hands-on, detail-oriented individual to drive accuracy, efficiency, and scalability across the AP function. 

You will:

• Lead end-to-end AP operations including invoice processing, approvals, payments, accruals, and prepaids to ensure timely and accurate posting to the GL.
• Own month-end and year-end close procedures for AP, including reconciliations and cut-off controls, reducing post-close adjustments and supporting a clean trial balance.
• Prepare, review, and maintain audit-ready PBCs and serve as the primary AP subject matter expert for external auditors such as KPMG.
• Drive process improvements and automation initiatives to scale AP workflows, reduce manual effort, and strengthen internal controls.
• Partner with Corporate Accounting and FP&A to support accrual accuracy, cash forecasting, and timely resolution of vendor issues.
• Build standardized AP procedures and expectations, with future opportunity to mentor and manage additional AP resources as the function scales.
• Enhance automation and process efficiency by leveraging AI tools to streamline workflows, reduce manual effort, and improve accuracy and scalability across operations

You’d be a great fit if:

• You have 6+ years of accounting experience with 3+ years managing AP operations in a high-growth or complex environment (healthcare, fintech, or SaaS preferred).
• Proven experience with month-end/year-end close, reconciliations, and audit support.
• Strong knowledge of AP-related US GAAP (expense recognition, accruals, prepaids) and internal controls.
• Hands-on operator who can implement scalable processes and drive automation initiatives.
• Excellent communicator with strong interpersonal skills, able to collaborate with cross-functional partners and vendors.
• Passionate about building reliable, efficient AP processes and developing team capabilities.
• Hands-on experience with NetSuite and Ramp, with the ability to optimize workflows and reporting within these systems.
• A curiosity into using AI tools and a dedication to leveraging AI for process automation and efficiency.

Compensation and Benefits:

The expected base pay range for this position is $110,400- $172,500, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

As Senior Counsel, Regulatory, you will be a key strategic partner responsible for partnering with Product, Engineering, Operations, and Privacy teams to support innovation during a pivotal growth phase. This is a unique opportunity to join a mission-driven healthcare technology company where legal is viewed as a strategic partner rather than a roadblock. You will serve as the primary regulatory attorney and thought partner for Headway's Clinical and Operations teams, with particular focus on health laws and regulations that impact patient care and related build of innovative technology products. While we prefer candidates based in New York, we will consider exceptional candidates nationwide. 

• Serve as embedded regulatory thought partner to Clinical and Operations teams, providing real-time guidance on clinical practice, telehealth modalities, PC operations, and clinical regulatory implications for product development
• Partner with Clinical and Compliance team on policy development, audit response, and remediation strategies while providing legal interpretation of healthcare regulations
• Translate complex healthcare regulations into practical guidance and tools that Clinical and Operations teams can easily understand and implement
• Anticipate regulatory challenges and proactively develop solutions that enable business objectives while facilitating compliance
• Build strong relationships across teams to position regulatory guidance as a business enabler rather than an obstacle

You would be a great fit if you have:

• 5+ years of post-bar admittance legal experience with significant healthcare regulatory expertise, particularly in health technology, corporate practice of medicine, behavioral health clinical practice, and CPOM
• Deep understanding of multi-state healthcare regulations (e.g. telehealth) in evolving regulatory environments
• Experience serving as a trusted advisor to Clinical, Operations and/or Compliance teams in a healthcare technology environment
• Proven ability to translate complex healthcare regulatory requirements into clear, actionable guidance for non-legal stakeholders
• Track record of balancing compliance obligations with business objectives in fast-paced organizations
• Strong communication skills and political savvy to navigate competing priorities and build effective partnerships
• JD from accredited law school and active bar membership in good standing (ability to register as NY in-house counsel required)

Compensation and Benefits:

The expected base pay range for this position is $179,200 - $280,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
  • Equity Compensation
  • Medical, Dental, and Vision coverage
  • HSA / FSA
  • 401K
  • Work-from-Home Stipend
  • Therapy Reimbursement
  • 16-week parental leave for eligible employees
  • Carrot Fertility annual reimbursement and membership
  • 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
  • Flexible PTO
  • Employee Assistance Program (EAP)
  • Training and professional development

Headway is seeking a Manager, Revenue Accounting to help lead and scale the revenue accounting function. In this role, you will translate the revenue accounting strategy set by the Director of Revenue Accounting into a best-in-class operating model. You will own the day-to-day execution of revenue accounting, lead and develop a team of Senior Revenue Accountants, and drive continuous improvements across processes, systems, and controls.

This is a highly cross-functional role partnering with Finance, Legal, Data, Engineering, Product, and Operations on revenue-impacting initiatives. This role offers the opportunity to have a meaningful impact on how revenue is accounted for, reported, and scaled at Headway.

You will:

• Own the operational execution of the revenue accounting function, ensuring accurate, timely, and compliant revenue reporting under ASC 606
• Lead and develop a team of Senior Revenue Accountants, setting clear expectations, coaching for growth, and building a high-performance culture
• Drive the revenue month-end close process, ensuring consistent, timely delivery and continuous improvement in close quality and efficiency
• Serve as a thought partner to the Director of Revenue Accounting by surfacing operational insights, risks, and improvement opportunities that inform the revenue accounting strategy
• Elevate issues, patterns, and opportunities observed in execution into clear, actionable input that informs strategic decisions for the revenue accounting function
• Partner cross-functionally on revenue-impacting initiatives, serving as a key operational lead to ensure alignment and effective delivery
• Oversee the design, implementation, and maintenance of scalable revenue processes, policies, and internal controls
• Identify and drive process improvements through automation, system enhancements, and data-driven insights
• Drive the adoption of AI and automation across revenue accounting processes to improve scalability, accuracy, and efficiency
• Play a key role in audit readiness and execution for revenue, including reviewing support, resolving issues, and strengthening documentation

You’d be a great fit for this role if:

• You have 5-7+ years of accounting experience, including significant experience in revenue accounting at high-growth companies
• You have 2-3+ years of experience managing or leading others, with a demonstrated ability to develop talent and drive results through teams
• Strong working knowledge of ASC 606, with hands-on experience applying revenue guidance in practice
• You have experience operating in fast-paced, cross-functional environments with evolving systems and processes
• You are both highly detail-oriented and comfortable operating at a higher level, connecting execution to business outcomes
• You are an excellent communicator who can translate complex accounting topics for non-accounting partners
• You bring a builder mindset and enjoy creating structure, clarity, and scalable solutions
• You are a CPA with Big 4 and/or high-growth company experience

Compensation and Benefits:

The expected base pay range for this position is $110,400 - $172,500, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

#LI-LN1

About the team

The Ranking & Relevance team’s mission is to help every patient find the right provider for their needs. We are building the matching system that powers this connection, from search and discovery to ranking and personalization. Our goal is to combine cutting-edge machine learning with a deep understanding of patient and provider experience.

About the role

We are looking for a Senior Machine Learning Engineer to be a core contributor to Headway's ranking and relevance systems. You will design, build, and ship ML models that determine how patients discover and connect with therapists — using search, recommendation, and personalization techniques to improve matching quality across the care journey.

In this role, you will work with significant autonomy on scoped problem areas, contribute to technical direction, and collaborate closely with product, engineering, and data science to drive measurable outcomes for patients and providers.

What you’ll do

At Headway, one of our most important challenges is ensuring that patients find the right therapist quickly and effectively. We are investing deeply in search, ranking, and relevance systems powered by machine learning. As a Senior Machine Learning Engineer, you will focus on:

• Matching and ranking: Build and iterate on ML models that power how patients discover and connect with providers — from candidate generation to final ranking.
• Personalization: Leverage patient signals, provider attributes, and outcomes data to improve matching accuracy and relevance over time.
• Model development end-to-end: Own the full lifecycle of models you build — from offline evaluation and experimentation to production deployment and monitoring.
• Experimentation: Design and analyze A/B tests, define the right offline proxies and online metrics, and translate results into product decisions.
• Cross-functional collaboration: Partner with product managers, software engineers, and data scientists to scope problems, align on success metrics, and ship improvements that move the needle for patients.
• Raising the bar: Contribute to ML best practices on the team — through code reviews, documentation, and sharing what you learn from the systems you build.

Who you are

• You have 5+ years of experience in applied ML roles, with at least 3 years of meaningful hands-on modeling work in ranking, relevance, recommendations, search, or personalization.
• You are fluent in Python and experienced with ML frameworks such as TensorFlow, PyTorch, Scikit-learn, or CatBoost.
• You have taken ML models from prototype to production and understand what it takes to make them reliable, maintainable, and performant at scale.
• You are comfortable designing and running A/B experiments, selecting appropriate metrics, and interpreting results with rigor.
• You bring product intuition alongside technical depth — you care about making the patient experience meaningfully better, not just improving an offline metric.
• You work well in collaborative, cross-functional environments and can communicate technical tradeoffs clearly to non-ML stakeholders.

Nice to have

• Experience with search, discovery, matching systems or consumer facing personalization.
• Familiarity with modern retrieval techniques (vector search, embeddings, semantic search).
• Exposure to ML infrastructure such as feature stores, model monitoring, and retraining pipelines.
• Experience with Metaflow, SageMaker, and Outerbounds.
• Background in healthcare, marketplace, or other B2C domains where user-provider or user-product fit is the core product problem.

Our interview process

After you apply to Headway, here are some details of what to expect during the interview process.

1. Initial screen: You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background.
2. First round: You’ll meet with an engineer on the team to do some live coding and learn more about the engineering team.
3. Final rounds: You’ll meet several more team members for technical and non-technical interviews and leave with a fuller picture of what it’s like to work at Headway.
4. References and the offer: Our favorite part of the process. We’ll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members.

Compensation and Benefits:

The expected base pay range for this position is $218,500 - $273,125, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

Patients are at the center of Headway’s mission — and analytics plays a critical role in how we serve them. As the Director of Data Science, Patient you will lead the data science organization that helps Headway build an extraordinarily successful consumer brand and patient marketplace, with a relentless focus on measurable growth and patient impact. You will be the data science peer to senior leaders across Product, Growth Marketing, Operations, Finance, and Clinical, and you will set the standards and direction for how we evaluate acquisition, conversion, retention, and outcomes. This is a senior leadership role for a driver who can turn ambiguity into clarity, build a high-performing team, and create the insight engine that makes a consumer healthcare business win.

In this role, you will: 

Shape a world-class patient product experience

• Partner with product, engineering, and operations to deeply understand the patient journey and identify the highest-leverage opportunities to improve discovery, conversion, and cures.
• Lead the analytics approach for product changes: clarify goals, define success metrics and guardrails, diagnose trade-offs, and ensure learnings drive roadmap decisions.
• Build strong segmentation and cohort understanding to explain who we serve best, where drop-offs happen, and what experiences drive long-term value.

Build the patient growth and marketing analytics engine

• Own the analytics strategy for consumer acquisition and performance marketing, ensuring we can evaluate channel effectiveness, creative performance, conversion quality, CAC efficiency, and incrementality.
• Partner with Growth Marketing and Finance to improve budget allocation decisions through clear measurement, forecasting inputs, and crisp performance narratives.
• Establish an operating cadence that makes marketing performance, funnel health, and unit economics legible to leaders, and turns weekly learning into action.

Run a high-velocity learning system

• Establish a rigorous experimentation culture across marketing and product, including clear hypotheses, fast iteration loops, strong guardrails, and decision-oriented readouts.
• Create repeatable “insight to action” mechanisms: standardized deep dives, performance narratives, and decision memos that accelerate leadership alignment.

Scale an elite team

• Lead, coach, and develop a team of data scientists and data science managers; set clear expectations for ownership, communication, and impact.
• Recruit and retain world-class talent and build an org structure that scales from 6 - 8 people to roughly double that size through 2026.
• Build strong managers and tech leads, and create a culture that is rigorous, curious, and relentlessly focused on business outcomes.

Own standards for truth and clarity

• Define and enforce metric standards across the patient funnel so teams align on what matters and can confidently compare performance over time.
• Ensure stakeholders have trustworthy self-serve reporting and clear definitions, minimizing time spent debating numbers.

Marketing analytics priorities (core to the role)

• Performance marketing measurement: channel performance, creative learning, funnel conversion, landing experiences, and attribution.
• Incrementally and causal measurement: designing tests and analyses that distinguish correlation from true impact.
• Budget and efficiency narratives: CAC, payback, cohort quality, saturation effects, and marginal ROI.
• Growth diagnostics: identifying why performance changed, what levers matter, and what actions will improve results.

You'll be a great fit if:

• You have 10+ years of experience in data science/analytics, growth analytics, marketing analytics, product analytics, or data-driven strategy, including 6+ years leading and scaling teams.
• You have built analytics that materially improved consumer growth outcomes: acquisition efficiency, conversion, retention, and product-led expansion.
• You have strong marketing analytics instincts and can partner credibly with Growth leaders on channels, creative, attribution, and incrementality.
• You can translate messy consumer journeys into clear metrics, crisp narratives, and high-quality decisions, without slowing teams down.
• You are an exceptional leader and coach with a track record of hiring world-class talent and building high-performance teams.
• You bring intellectual honesty and strong judgment, and you can push back when measurement is weak or narratives are wrong.
• You have deep expertise in experimentation design, statistical inference, and causal methods such as CUPED, diff-in-diff, synthetic controls, or propensity modeling
• Experience partnering cross functionally to drive measurable improvements in user experience or product performance
• Comfort with ambiguity and a bias toward action, clarity, and iteration
• You are motivated to advance Headway’s mission to make mental healthcare more accessible and affordable across the United States

Compensation & Benefits:

The expected base pay range for this position is $249,600 - $312,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

#LI-AC1

As Senior Counsel, Labor & Employment, you will be the lead attorney partnering with Headway’s People function to support a rapidly growing and national workforce. You will own day-to-day advice and counsel on employment matters while also working closely with the People team to enhance systems and processes to allow Headway to scale with speed and fidelity.  This is a unique opportunity to join a mission-driven healthcare technology company, work alongside passionate and talented colleagues, and grow in an environment where Legal is viewed as a strategic partner.

You will:

• Serve as the primary legal advisor to the People team and business leaders on the full range of L&E matters, including hiring practices, performance management, separations, leaves and accommodations, investigations, wage and hour compliance, and other key areas  
• Build L&E infrastructure – design and review People-related policies, procedures, and workflows to enhance efficiency and effectiveness
• Be the in-house subject matter expert, training HRBPs and People managers on L&E developments and best-practices
• Draft, review, and negotiate employment-related agreements and documents
• Represent the company, including managing outside counsel, in litigation and related disputes  

You’d be a great fit if:

• You have 5+ years of post-bar admittance legal experience with a deep understanding of L&E matters 
• You have meaningful in-house experience in a fast-paced, high-growth start-up environment
• You have a deep ability to build relationships and consensus with colleagues amid competing views 
• You have detail-obsession that drives clarity – without missing the forest for the trees
• You have a J.D. from an accredited law school and active bar membership in good standing (including ability to register as NY in-house counsel)

While we prefer candidates based in the New York metro area, we will consider exceptional candidates nationwide.

Compensation and Benefits:

The expected base pay range for this position is $179,200 - $280,000 based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

#LI-LN1

About this role: 

Building for trust is non‑negotiable in our mission of making mental healthcare more accessible and affordable across the US: patients share sensitive information, payers demand demonstrably strong controls, and providers depend on reliable, secure infrastructure. Trust Foundations is responsible for instilling confidence in our products by safeguarding our user’s data. We achieve this by developing out-of-the-box identity, access, and secure-data platforms for other engineering teams to utilize. Our mission is to make the most secure path the most efficient path, enabling clinicians, patients, and payers to trust Headway implicitly.

This team is growing and we are hiring for multiple roles at both mid/senior levels. As a Software Engineer/Senior Software Engineer on our Trust Foundations team, you’ll be working on 0-1 access control (RBAC/ABAC), OAuth 2.0/OIDC platforms while shaping the long‑term vision for trust at Headway. You will translate open identity and authorization standards into scalable building blocks; embed privacy‑by‑design and reliability principles into everything we build; and mentor engineers across the company in Trust first thinking.

What you’ll do here:

• Design, build, and operate core trust primitives - authentication providers, authorization engines, data governance, stratified encrypted data stores, and tamper‑evident audits.
• Embed security & privacy by design - Partner with Legal / Compliance to translate regulatory language into concrete engineering controls.
• Scale our identity rails -  Design and evolve multi‑tenant authentication & authorization services that handle millions of sessions daily with high availability expectations.
• Deliver scalable, secure platform foundations -  Design and build 0-1 shared services, implement consistent access control patterns that enable product teams to move quickly while ensuring security-by-default (least‑privilege access, encryption in transit and at rest, audit hooks).
• Turn ambiguous requirements into incremental delivery plans - Lead architecture reviews; break large problems into testable milestones; and make pragmatic build‑vs‑buy decisions in a regulated domain.
• Champion operational excellence - Instrument services, tune alerting, own on‑call runbooks, and drive post‑incident hardening.
• Elevate engineering culture -  Mentor teammates, document patterns, and help recruit the next generation of Headway engineers.

Who you are: 

• Security Mindset: You are passionate about cybersecurity and protecting access to sensitive user data. 
• Cross functional Collaboration - you have demonstrated effective collaboration working with product, infosec and compliance teams. 
• A track record of mentoring engineers, elevating design quality, and improving engineering processes.
• Secure Architecture: You think of security platforms, not as a gate, but as an enabler of secure product development. 
• Dealing with ambiguity: You are comfortable working with and bringing clarity to ambiguous requirements. 

Preferred (not required) experience: 

• 3+ years of experience working in data governance and access control systems (RBAC/ABAC) compliant with HIPAA, HITRUST, SOC2 etc
• 3+ years of experience working with third party IdPs and expertise with OAuth 2.0 / OIDC standards.
• 3+ years of experience with Python, TypeScript and AWS.

About Engineering at headway:

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide.  The engineering team at Headway is a small but mighty team using technology to build that future (and have a fun time while doing it!).

Principles that guide us:

• Focus on the mission - We view software as a means of effecting change in the world, not as an end unto itself. We write software to empower our patients and therapist to better solve the problems they’re facing.
• Ship small, learn fast - We are building new and novel products and believe that we learn what our users need by quickly shipping and iteration.
• Everything is a product - Whether it's our patient search experience or a developer productivity improvement, we treat everything we build at Headway as a product with end-users in mind.
• Optimize for trust - We believe that engineers should be continually learning. To learn effectively and to be productive, engineers must feel safe asking questions and discussing mistakes.

Tools we use:

• Languages: Python 3, TypeScript
• Libraries & Frameworks: FastAPI, SQLAlchemy, React, Remix, Next.js
• Datastores: Postgres, Redis
• Infrastructure: AWS (Fargate, ECS, S3, and more), Spark and Kafka
• Monitoring: Datadog, PagerDuty, Sentry
• Version Control: Github, PagerDuty
• Vulnerability Management: Snyk, Semgrep
• Cloud Security: Lacework

Our interview process

After you apply to Headway, here are some details of what to expect during the interview process.

• Initial screen: You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background. 
• First round: You'll meet with an engineer on the team to do some live coding and learn more about the engineering team.
• Final rounds: You’ll meet several more team members for technical and non-technical interviews and leave with a fuller picture of what it’s like to work at Headway.
• References and the Offer: Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!

Compensation and Benefits:

The expected base pay range for this position is $168,300 - $237,500, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

Equity Compensation

• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

#LI-SC1

At Headway, our mission is to build a new mental healthcare system that everyone can access. Behind the magic for patients to find right and predictable care is our robust design system, insurance platform and internal tools. 

As the Product Design Director for this team, you will help contribute to our mission by making Headway’s operation more efficient, by building a powerful design system, strategic content design, wildly predictable insurance experience and robust internal tools. In this role, you will lead and continue building a talented team of product designers, design system designers and content designers. You'll be a key partner to other teams, ensuring our design systems empower teams to build cohesive, high-quality experiences at scale.

In this role, you will:

• Lead the design systems across our products, as well as lead the team defining these systems. You will also be an advocate of design craftsmanship across our product, design, and engineering organizations.
• Oversee the foundational experiences including insurance experiences, support experiences and security experiences for our customers.
• Manage the internal tooling experiences that helps Headway operate efficiently.
• Hire, lead, and coach a team of design system designers, content designers, and product designers responsible for design systems and foundational experiences.

Experience we're seeking:

• 3+ years of experience leading successful design system or product design teams.
• Extensive experience in building and shipping design systems across a variety of systems.
• Experience building and scaling a design team.
• Great communication and excel in making complex technical details easy to understand.
• Value high quality visual design with attention to detail.

Compensation and Benefits:

The expected base pay range for this position is $249,600 to $312,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

#LI-RJ1

About Engineering at Headway

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide.

Principles that guide us:

• Focus on the mission: We view software as a means of effecting change in the world, not as an end unto itself. We write software to empower our patients and therapist to better solve the problems they’re facing. 
• Ship small, learn fast: We are building new and novel products and believe that we learn what our users need by quickly shipping and iteration
• Everything is a product: Whether it's our patient search experience or a developer productivity improvement, we treat everything we build at Headway as a product with end-users in mind.
• Optimize for trust: We believe that engineers should be continually learning. To learn effectively and to be productive, engineers must feel safe asking questions and discussing mistakes.

Tools we use:

• Languages: Python 3, TypeScript
• Libraries & Frameworks: FastAPI, SQLAlchemy, React, Remix, Next.js
• Datastores: Postgres, Redis
• Infrastructure: AWS (Fargate, ECS, S3, and more), Spark and Kafka
• Monitoring: Datadog, PagerDuty, Sentry
• Version Control: Github, PagerDuty
• Vulnerability Management: Snyk, Semgrep
• Cloud Security: Lacework

About these roles

At Headway, we’re building a national network of therapists who accept insurance — and making mental healthcare radically more accessible in the process. Supporting providers isn’t just about connecting them with patients — it’s about delivering the tools they need to manage their practice with ease, confidence, and compliance.

Our providers are the heart of Headway’s mission — and empowering them with an easy-to-use platform is critical to both their success and the quality of care patients receive. Whether it’s saving providers time, simplifying documentation, or ensuring compliance, this role is at the center of our providers’ lives. As an engineering leader at Headway, you will be responsible for leading and growing the engineering pods behind our provider experiences through people development, strategic planning, and hands-on technical support or guidance. You get to play a leading role in defining what and how these teams build, setting up how the teams operate, support, and ultimately drive best-in-class user experiences that have a measurable impact on our ability to execute and meet the demands of a high growth startup. 

We are hiring for 3 Engineering Managers within the Provider group -

Group Practices EM: Group Practices represents a substantial portion of our provider network and have specific needs to run their practice. This team is responsible for continuing to grow the Group Practices segment and enabling group practice providers and their administrative staff to operate efficiently on Headway.

CHART EM: Responsible for ensuring providers have the tools they need to efficiently document their clinical care. From AI-supported clinical documentation features, to tools for psychiatrists to manage their patient's medications, this team is streamlining the way therapists record their care.

Practice Foundations EM: We are evolving how we support a highly diverse provider network. Providers work in very different ways, and this team is responsible for building differentiated experiences that meet providers where they are, while also encouraging high-quality care and strong engagement with the Headway platform

Who you are

We’re looking for experienced engineering team leaders and people managers who are product-minded, data-informed, and energized by growth. As an Engineering Manager at Headway, you will work closely with Engineering Leadership, Product, Marketing, RevOps, and Design to shape the future of our provider acquisition strategy. This is an exciting opportunity for a passionate, mission-aligned engineering leader to make an immediate impact at a high-growth company.

• Lead and manage an engineering team focused on provider acquisition and growth (starting with 2–3 engineers and scaling over time)
• Partner closely with cross-functional stakeholders to build systems that enable rapid experimentation and long-term scale
• Collaborate with the Onboarding team to ensure a seamless end-to-end provider experience from first touch to first appointment
• Drive alignment across your team on process, prioritization, and product outcomes
• Develop and grow your team through weekly 1-1s, mentorship, and feedback
• Work with and help develop aspiring engineering leaders within the engineering team
• Contribute to the broader company strategy and product roadmap

Below are additional experiences we think help engineering managers succeed at Headway:

• You have 3+ years of experience as an experienced Engineering Manager
• You have 3-5+ years of experience as a Software Engineer
• You’re energized by experimentation and growth — and can balance short-term learning with long-term scale
• You have a strong product mindset and have built strong cross-functional relationships that drive optimal user experiences and build trust with users
• You have a strong technical foundation that allows you to ensure your team is making appropriate technical decisions
• You have a track record of building and leading high performing teams that have effectively delivered business outcomes through technical investments
• You have a track record of working well across teams and functions
• Nice to have: Prior experience with Python and React and working with AWS infrastructure
• Nice to have: Experience in health tech, building user-facing products
• BS, MS in Computer Science or related field

Our interview process

After you apply to Headway, here are some details of what to expect during the interview process.

• Initial screen: You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background. 
• First rounds: You'll meet with an engineering leader on the team to go deeper into your team and people leadership experiences and complete one technical (systems design) interview.
• Final rounds: You’ll meet team members across product and engineering leadership for multiple behavioral interviews, leaving you with a fuller picture of what it’s like to work at Headway.
• References and the Offer: Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!

Compensation and Benefits:

The expected base pay range for this position is $190,000 - $237,500, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

• Equity Compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About Engineering at Headway

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide. The engineering team at Headway is a small (~120) but mighty team using technology to build that future (and have a fun time while doing it!).

Principles that guide us:

• Focus on the mission: We view software as a means of effecting change in the world, not as an end unto itself. We write software to empower our patients and therapist to better solve the problems they’re facing. 
• Ship small, learn fast: We are building new and novel products and believe that we learn what our users need by quickly shipping and iteration
• Everything is a product: Whether it's our patient search experience or a developer productivity improvement, we treat everything we build at Headway as a product with end-users in mind.
• Optimize for trust: We believe that engineers should be continually learning. To learn effectively and to be productive, engineers must feel safe asking questions and discussing mistakes.

Tools we use:

• Languages: Python 3, TypeScript
• Libraries & Frameworks: FastAPI, SQLAlchemy, React, Remix, Next.js
• Datastores: Postgres, Redis
• Infrastructure: AWS (Fargate, ECS, S3, and more), Spark and Kafka
• Monitoring: Datadog, PagerDuty, Sentry
• Version Control: Github, PagerDuty
• Vulnerability Management: Snyk, Semgrep
• Cloud Security: Lacework

About this role

This role sits at the intersection of growth, product development, and marketing. You’ll have the freedom to innovate and experiment while collaborating with a diverse group of cross-functional partners from across the company. This is an opportunity to tackle complex, rewarding problems in a highly collaborative, supportive environment that values technical excellence and operational rigor. You’ll build systems that help patients discover and access mental health care, directly improving lives and transforming the healthcare landscape. Your work in this role will shape how thousands of patients connect with care, making a lasting impact on Headway’s mission to reimagine mental healthcare access for all.

As an engineering leader at Headway, you will be responsible for leading and growing the team behind these core growth initiatives through people development, strategic planning, and hands-on technical support. You’ll play a leading role in defining what and how these systems are built, setting up how the team operates, and ultimately driving best-in-class experiences that convert interest into action.

This is a critical leadership role for Headway and our mission to make mental healthcare more accessible. 

Provider Growth Pod

Supporting providers isn't just about connecting them with patients — it starts much earlier, with helping them discover Headway and understand the value we provide. Our providers are at the heart of Headway's mission — and enabling more of them to join our platform is critical to expanding access to care. This role is focused on building the tools, systems, and experiences that help providers learn about Headway, express interest, and begin their journey. From our referral engine and marketing web experiences to lead capture and routing infrastructure, you'll be responsible for the end-to-end technical foundation that drives provider acquisition. By helping more providers discover, trust, and join Headway, you'll directly impact both provider supply and patient access.

Who you are

We're looking for experienced engineering team leaders and people managers who are product-minded, data-informed, and energized by growth. As an Engineering Manager at Headway, you will work closely with Engineering Leadership, Product, Marketing, Design, Data, and RevOps to shape the future of our growth strategy. This is an exciting opportunity for a passionate, mission-aligned engineering leader to make an immediate impact at a high-growth company.

Responsibilities:

• Lead and manage an engineering team focused on growth
• Partner closely with cross-functional stakeholders to build systems that enable rapid experimentation and long-term scale
• Partner closely with Product, Design, Marketing, Data to rapidly iterate through A/B testing
• Collaborate with activation and onboarding teams to ensure a seamless end-to-end user experience from first touch to first appointment
• Drive alignment across your team on process, prioritization, and product outcomes
• Develop and grow your team through weekly 1-1s, mentorship, and feedback
• Work with and help develop aspiring engineering leaders within the engineering team
• Contribute to the broader company strategy and product roadmap
• Help build out our engineering team as our headcount grows from 120 to 175+ through the remainder of the year

Below are additional experiences we think help engineering managers succeed at Headway:

• You have 3+ years of experience as an Engineering Manager at a high-growth startup or scale-up, building and leading high performing teams that have effectively delivered business outcomes through technical investments
• You have 5+ years of experience as a Software Engineer
• You're energized by experimentation and growth — and can balance short-term learning with long-term scale
• You have a strong product mindset and have built strong cross-functional relationships that drive optimal user experiences and build trust with users
• You have a strong technical foundation that allows you to ensure your team is making appropriate technical decisions
• You are flexible and adaptable; you understand that the best growth teams must learn and iterate quickly, and that growth roadmaps are dynamic as a result
• Nice to have: Prior experience with SEO and paid advertising
• Nice to have: Prior experience with Python and React and working with AWS infrastructure
• Nice to have: Experience in health tech, building user-facing products
• BS, MS in Computer Science or related field

Our interview process

After you apply to Headway, here are some details of what to expect during the interview process.

• Initial screen: You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background. 
• First rounds: You'll meet with an engineering leader on the team to go deeper into your team and people leadership experiences and complete one technical (systems design) interview.
• Final rounds: You’ll meet team members across product and engineering leadership for multiple behavioral interviews, leaving you with a fuller picture of what it’s like to work at Headway.
• References and the Offer: Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!

Compensation and Benefits:

The expected base pay range for this position is $190,000 - $237,500, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

As Senior Counsel, Commercial, you will be the Legal partner to Headway’s best-in-class Payer contracting team, negotiating innovative and high-impact partnerships with the nation’s leading health plans. You will also be responsible for building out systems and processes that will allow the Legal and Payer teams to partner most effectively.  This is a unique opportunity to join a mission-driven healthcare technology company, work alongside passionate and talented colleagues, and grow in an environment where Legal is viewed as a strategic partner.  

You will:

• Own our payer contracting strategy, aligning business interests with legal terms and regulations
• Build for scale and implement systems to land high-value payer contracts efficiently 
• Review and negotiate the terms of Headway’s health plan agreements
• Partner with outside counsel on cutting-edge approaches to unlock value and mitigate risk 

You’d be a great fit if:

• You have 5+ years of post-bar admittance legal experience with a deep understanding of healthcare contracting between payers and providers 
• You have meaningful in-house experience in a fast-paced, high-growth start-up environment
• You have a deep ability to build relationships and consensus with colleagues amid competing views and priorities
• You have a builder’s mindset, and are energized by enhancing operational structure
• You have a J.D. from an accredited law school and active bar membership in good standing required  (including ability to register as NY in-house counsel)

Compensation and Benefits:

The expected base pay range for this position is $179,200 - $280,000 based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

#LI-LN1

Creative at Headway isn’t just about making things sound good. It’s the strategic engine that shapes how we communicate, build trust, and help people take meaningful steps toward care. Our team of Art Directors, Brand Designers, Writers, Content Leads, and Creative Ops partner closely to deliver work that strengthens the brand while driving real business impact.

As an Associate Creative Director, Copy, you are both a creative leader and a hands-on partner in the work. You’ll help define how Headway sounds across campaigns, growth initiatives, and key brand moments while overseeing our content efforts to ensure clarity, consistency, and craft at scale. This role blends big-idea thinking, people leadership, and day-to-day creative direction, ensuring every word reflects the care, credibility, and humanity at the core of our mission.

What you'll do:

• Lead copy direction across brand and growth campaigns, launches, and key initiatives.
• Shape and steward Headway’s brand voice, tone, and messaging across channels.
• Support our content and editorial team, ensuring alignment with brand standards and creative direction.
• Partner closely with senior creative leaders, Art Directors, and Designers to develop impactful and emotionally resonant ideas.
• Grasp the creative brief for the core insight, and translate marketing and business priorities into clear, compelling creative strategies and executions.
• Guide writers through concepting, iteration, and execution with thoughtful, actionable feedback.
• Act as a brand steward, collaborating with cross-functional partners to maintain clarity and consistency.
• Mentor and develop writers and creatives, fostering a culture rooted in craft, curiosity, and collaboration.
• Work closely with Creative Ops to ensure ideas are executed with quality, intention, and efficiency.

What we're looking for:

• 8+ years of experience copywriting and creative leadership, across brand and growth work (agency and/or in-house).
• A portfolio that demonstrates strong campaign thinking, voice development, and exceptional writing craft.
• A clear point of view on taste, storytelling, and what makes creative effective.
• Comfort balancing strategic leadership with hands-on creative direction.
• Experience overseeing or partnering closely with content and editorial teams is a strong plus.
• Confidence presenting and articulating creative rationale to both creative and non-creative audiences.
• A collaborative and growth mindset- you enable others to do their best work.

Compensation and Benefits:

The expected base pay range for this position is $169,000 - $212,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

#LI-RJ1

To power this mission, we're building a world-class Operations team that enables efficiency, growth, and quality. As a member of this team, you will have a material impact on the trajectory of Headway and own workflows and processes that are core to the impact we deliver for our patients, providers, and payer partners.

As a Senior Operations Associate, you will operationalize and scale core workflows that will deliver real-world impact to hundreds of thousands of patients and providers around the country. You will be responsible for designing and implementing world-class execution strategy to ensure high-quality operations and you will also be an operational bridge to our product and data teams at Headway in order to drive the future-first nature of the solutions you deliver. 

This role is core to ensuring the operational health of our business and will provide you with deep exposure to the unique mechanics of the healthcare system. This is an opportunity to get hands-on in a data- and product-first environment and own outcomes core to the success of our business. 

• You Will: 
• Drive the build, execution, monitoring & ongoing implementation of scalable products and processes that enable us to deliver on core business challenges
• Leverage your operational expertise to identify opportunities for improved efficiency and automation
• Support and lead cross-functional efforts with our product, engineering, payer, and CX teams to drive core ops processes and achieve team OKRs.

• You’d be a great fit if…
• You have 3-5 years of experience in consulting / operations / investment banking or related experience; operations experience at a high-growth startup is a plus.
• You are a self-starter, and are constantly pushing toward clarity and execution.
• You are highly data-driven and can drive complex analyses to identify key actionable insights.
• You are a collaborator who proactively partners across teams while holding others and yourself accountable for business results.
• You are a systems thinker, inclined to solve problems with product and automation.

Compensation and Benefits:

The expected base pay range for this position is $76,160 - $112,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development