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

This role exists to build a growth engine that compounds. You will be responsible for scaling Headway-sourced patients. This begins with high confidence in incrementally, while building the people, tooling, and creative systems that will ultimately make results repeatable.

Reporting directly to the GM of Patient, you will be the first senior growth marketing hire in Headway’s history on the patient side. You will own the full patient growth marketing remit across paid, lifecycle, and organic channels; stand up foundational martech and measurement systems; deploy creative systems that increase testing velocity; and partner across the marketplace to drive outcomes without channel cannibalization.

You’ll work closely with key partners across Engineering, Creative, Data Science/Analytics, Finance, Business Ops, and Provider Marketing, while helping define the long-term strategy for patient growth and broader marketplace dynamics.

What You’ll Do...

• Patient growth marketing: Own paid acquisition (Search, Social, OLV/OTT, Programmatic/Display), Lifecycle (email/SMS/push), and Organic (SEO, content distribution, Reddit/IG/TikTok/YouTube).
• Martech & measurement: Lead channel plumbing, experimentation frameworks, attribution, incrementality, MMM, and reporting — co-owning approach with Eng and Data but owning the outcomes.
• Creative systems for growth: Drive briefing, testing velocity, and learning loops across message × audience × asset × surface.
• Cross-marketplace levers: Align patient and provider growth to prevent channel overlap and unlock network effects.
• Team building: Hire, lead, and develop a high-bar, technical, and creative team across paid, lifecycle, and organic.
• Partner cross-functionally: Work with Product/Eng to build surfaces that drive conversion and quality, not just spend.

You’ll Be a Great Fit If You…

• Have deep expertise in growth marketing with explicit experience in Google, Meta, and OTT/OLV channels.
• Have led lifecycle marketing teams and understand how best to deploy email, SMS, and push channels.
• Bring strong martech and attribution experience, including build vs. buy decisions and measurement frameworks (attribution, incrementality, MMM).
• Have partnered closely with Engineering and Product, operating as one team with shared outcomes.
• Have experience deploying AI-forward marketing strategies and maintain personal interest in AI-native marketing stacks.
• Communicate clearly and simply, translating complex performance marketing topics for non-experts, executives, and boards.
• Can build strategies grounded in business outcomes and understand tradeoffs across product, engineering, and operations.
• Have hired and led growth marketing teams of 20+ and built 0→1 systems at scale.
• Work effectively with diverse cross-functional partners across analytics, finance, sales, creative, product, and engineering.

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.

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 reimbursement and membership
• 13 paid holidays + company holiday break
• Flexible PTO
• EAP
• Training and professional development

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience.

Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

Headway participates in E-Verify. To learn more, click here.

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

Two Chairs is building a new kind of mental health system based on the idea that the status quo isn’t good enough. Industry-best clinician experiences, better client outcomes, groundbreaking innovation, and access to the highest quality care are how we’ll raise the bar for the entire industry. With that, we're excited and honored to have been recognized as a 2025 Great Place to Work and 2025 Fortune's Best Workplaces in Healthcare.

One of our company values is "Embrace Differences" and diversity, equity, inclusion, and belonging are the principles guiding how we build our business and teams. We encourage interested candidates from all backgrounds to apply even if they don't think they meet some expectations of the role.

Why Two Chairs is consistently a Great Place to Work 

• Consistent Pay: Earn an hourly rate of $62-$96 with semi-monthly pay. This is based on clinical experience, place of residence, and overall qualifications. Guaranteed base rate with incentive potential after initial ramp period.
• Truly Flexible Work: Work remotely with a schedule that fits your life: no nights, no weekends, no on-call responsibilities. We also provide paid administrative time so documentation doesn’t follow you home.
• Mission-Driven, Clinician-Led: We’re dedicated to creating a world where everyone has access to exceptional mental healthcare. Clinical decisions are made by clinicians for clinicians, ensuring you’re supported by a team that is focused on centering the client and enabling clinicians to deliver exceptional care.
• Clinical Excellence Comes First: You’ll join a deeply collaborative environment, with access to physician partners, therapists, and crisis support services. Our integrated platform provides tools that enable measurement-based care, clinical decision support, and seamless information sharing.

What You’ll Do

• Conduct 60-minute psychiatry assessments and 30 minute follow-up sessions remotely.
• Prescribe and manage psychiatric medications, including controlled substances, in accordance with state and federal regulations.
• Integrate brief psychotherapy when clinically appropriate to support your clients in reaching their goals efficiently and sustainably.
• Collaborate with physicians and clinical leadership for support, escalation, and continued learning.
• Partner with therapists and other providers through integrated care plans, shared treatment insights, and team consultation spaces.
• Use data-informed tools and measurement-based care to tailor treatment plans and improve outcomes.
• Contribute to a growing, diverse community of clinicians committed to redefining mental health care.

What success looks like

In your first 90 days

You will become comfortable with Two Chairs systems, processes, and teams, supported by an onboarding team and clinical leadership. You will gradually build a caseload and deliver exceptional mental health care. You will collaborate with team members and help refine workflows and care protocols. 

By the end of your first year

You will have established a robust caseload of clients and delivered exceptional care, as evidenced by clinical outcomes. You will have made contributions to our program and to a world where everyone has access to exceptional mental health care.

What We Offer

• Compensation you can count on:
• Competitive Pay: Hourly rate of $62-$96 based on clinical experience, place of residence, and overall qualifications
• Guaranteed Onboarding Support: 100% of hourly rate during your initial 90-day ramp period while you build your caseload
• Sustainable Base + Incentive: Following the ramp period, you’ll receive a guaranteed base (80% of your hourly rate) plus an incentive structure that rewards clinical productivity and the integration of psychotherapy.
• Comprehensive Coverage: we pay for administrative time, clinical consultations, trainings, and no-shows.
• Long-term Growth: Eligibility for annual performance-based merit increases
• Comprehensive Benefits:
• Sick leave
• Access to 401(k) retirement plan options
• Credentialing and cross-licensing support
• License renewal fee reimbursement
• Free Continuing Medical Education (CME) access
• Technology package including laptop, EHR system, HIPAA compliant video platform, and more
• Malpractice Insurance provided
• Flexible Schedule:
• Part-time, W2 position (up to 8 hours per week) with opportunity for increased hours over time. 
• Expect to spend ~75% of time on direct client care and ~25%  focused on admin/ supervisory work. The balance may vary based on team needs. 
• Build a schedule that works for you within our operating hours of M-F,  8am-8pm.
• Start date: mid-August 2026
• Clinical Coverage: 
• Backup coverage, so your clients are supported when you’re away
• Dedicated 24/7 crisis line available for immediate risk assessments and arrangement of in-person interventions if needed

Compensation Ranges

• Zone 1 / New York City and San Francisco | $80-108/hour
• New hires can reasonably expect an offer between $80 and $96/hour

• Zone 2 / Portland, Boston, Chicago, Washington DC, New Jersey, Washington,
  all other CA locations | $70-95/hour
• New hires can reasonably expect an offer between $70 and $86/hour

• Zone 3 / Miami, Philadelphia, Denver, Austin, Dallas, Houston | $67-91/hour
• New hires can reasonably expect an offer between $67 and $81/hour

• Zone 4 / All other locations | $62-87/hour
• New hires can reasonably expect an offer between $62 and $76/hour

Who You Are

• A board-certified Psychiatric Mental Health Nurse Practitioner (PMHNP-BC)
• 2+ years of experience providing mental health services as a PMHNP
• Licensed to practice in Washington as a PMHNP (additional licensure a plus!)
• Open to obtaining additional state licenses to support company expansion. Two Chairs covers all costs and provides full administrative support for the cross-licensing process.
• Active DEA license in Washington
• Experienced in delivering remote telepsychiatry services
• Passionate about high-quality, measurement-based, collaborative care
• Eager to join a community of clinicians who are driven by purpose and help us build upon our psychiatry program to improve our services and systems continually
• Able to start in mid-August 2026

Please stay alert for job scams: All communication will come from official Two Chairs email domains (@twochairs.com or @twochairscareers.com). See tips from the FTC to avoid job scams: https://www.consumeraffairs.com/news/ftc-offers-tips-on-avoiding-job-scams-041321.html 

#LI-REMOTE 

Two Chairs is building a new kind of mental health system based on the idea that the status quo isn’t good enough. Industry-best clinician experiences, better client outcomes, groundbreaking innovation, and access to the highest quality care are how we’ll raise the bar for the entire industry. With that, we're excited and honored to have been recognized as a 2025 Great Place to Work and 2025 Fortune's Best Workplaces in Healthcare.

One of our company values is "Embrace Differences" and diversity, equity, inclusion, and belonging are the principles guiding how we build our business and teams. We encourage interested candidates from all backgrounds to apply even if they don't think they meet some expectations of the role.

Why Two Chairs is consistently a Great Place to Work 

• Consistent Pay: Earn an hourly rate of $62-$96 with semi-monthly pay. This is based on clinical experience, place of residence, and overall qualifications. Guaranteed base rate with incentive potential after initial ramp period.
• Truly Flexible Work: Work remotely with a schedule that fits your life: no nights, no weekends, no on-call responsibilities. We also provide paid administrative time so documentation doesn’t follow you home.
• Mission-Driven, Clinician-Led: We’re dedicated to creating a world where everyone has access to exceptional mental healthcare. Clinical decisions are made by clinicians for clinicians, ensuring you’re supported by a team that is focused on centering the client and enabling clinicians to deliver exceptional care.
• Clinical Excellence Comes First: You’ll join a deeply collaborative environment, with access to physician partners, therapists, and crisis support services. Our integrated platform provides tools that enable measurement-based care, clinical decision support, and seamless information sharing.

What You’ll Do

• Conduct 60-minute psychiatry assessments and 30 minute follow-up sessions remotely.
• Prescribe and manage psychiatric medications, including controlled substances, in accordance with state and federal regulations.
• Integrate brief psychotherapy when clinically appropriate to support your clients in reaching their goals efficiently and sustainably.
• Collaborate with physicians and clinical leadership for support, escalation, and continued learning.
• Partner with therapists and other providers through integrated care plans, shared treatment insights, and team consultation spaces.
• Use data-informed tools and measurement-based care to tailor treatment plans and improve outcomes.
• Contribute to a growing, diverse community of clinicians committed to redefining mental health care.

What success looks like

In your first 90 days

You will become comfortable with Two Chairs systems, processes, and teams, supported by an onboarding team and clinical leadership. You will gradually build a caseload and deliver exceptional mental health care. You will collaborate with team members and help refine workflows and care protocols. 

By the end of your first year

You will have established a robust caseload of clients and delivered exceptional care, as evidenced by clinical outcomes. You will have made contributions to our program and to a world where everyone has access to exceptional mental health care.

What We Offer

• Compensation you can count on:
• Competitive Pay: Hourly rate of $62-$96 based on clinical experience, place of residence, and overall qualifications
• Guaranteed Onboarding Support: 100% of hourly rate during your initial 90-day ramp period while you build your caseload
• Sustainable Base + Incentive: Following the ramp period, you’ll receive a guaranteed base (80% of your hourly rate) plus an incentive structure that rewards clinical productivity and the integration of psychotherapy.
• Comprehensive Coverage: we pay for administrative time, clinical consultations, trainings, and no-shows.
• Long-term Growth: Eligibility for annual performance-based merit increases
• Comprehensive Benefits:
• Sick leave
• Access to 401(k) retirement plan options
• Credentialing and cross-licensing support
• License renewal fee reimbursement
• Free Continuing Medical Education (CME) access
• Technology package including laptop, EHR system, HIPAA compliant video platform, and more
• Malpractice Insurance provided
• Flexible Schedule:
• Part-time, W2 position (up to 8 hours per week) with opportunity for increased hours over time. 
• Expect to spend ~75% of time on direct client care and ~25%  focused on admin/ supervisory work. The balance may vary based on team needs. 
• Build a schedule that works for you within our operating hours of M-F,  8am-8pm.
• Start date: mid-August 2026
• Clinical Coverage: 
• Backup coverage, so your clients are supported when you’re away
• Dedicated 24/7 crisis line available for immediate risk assessments and arrangement of in-person interventions if needed

Compensation Ranges

• Zone 1 / New York City and San Francisco | $80-108/hour
• New hires can reasonably expect an offer between $80 and $96/hour

• Zone 2 / Portland, Boston, Chicago, Washington DC, New Jersey, Washington,
  all other CA locations | $70-95/hour
• New hires can reasonably expect an offer between $70 and $86/hour

• Zone 3 / Miami, Philadelphia, Denver, Austin, Dallas, Houston | $67-91/hour
• New hires can reasonably expect an offer between $67 and $81/hour

• Zone 4 / All other locations | $62-87/hour
• New hires can reasonably expect an offer between $62 and $76/hour

Who You Are

• A board-certified Psychiatric Mental Health Nurse Practitioner (PMHNP-BC)
• 2+ years of experience providing mental health services as a PMHNP
• Licensed to practice in Washington as a PMHNP (additional licensure a plus!)
• Open to obtaining additional state licenses to support company expansion. Two Chairs covers all costs and provides full administrative support for the cross-licensing process.
• Active DEA license in Washington
• Experienced in delivering remote telepsychiatry services
• Passionate about high-quality, measurement-based, collaborative care
• Eager to join a community of clinicians who are driven by purpose and help us build upon our psychiatry program to improve our services and systems continually
• Able to start in mid-August 2026

Please stay alert for job scams: All communication will come from official Two Chairs email domains (@twochairs.com or @twochairscareers.com). See tips from the FTC to avoid job scams: https://www.consumeraffairs.com/news/ftc-offers-tips-on-avoiding-job-scams-041321.html 

#LI-REMOTE

About This Role

We're looking for Staff PMs who are curious about what AI makes possible and eager to build in an environment where it's a core part of the toolkit — not a side project.

We are hiring across Patient, Provider, Payer, and Platform. The right candidates will bring strong product fundamentals and a willingness to build with AI in a regulated, high-stakes industry.  Staff PMs at Headway own product areas end-to-end: setting strategy, partnering deeply with engineering, data science, and design, and driving outcomes that move the company.

AI is changing how we build at Headway, and the size of opportunity for Headway to leverage AI is massive. We sit at the intersection of healthcare delivery, complex insurance systems, and a multi-sided marketplace serving tens of thousands of providers and millions of patients. AI is increasingly part of how we solve these problems — and we want PMs who are energized by that, whether they're deep in AI already or strong product thinkers ready to learn.

The Problems We're Solving

For Patients

Finding the right therapist, understanding your insurance benefits, and staying in care shouldn't be hard. Today it is. We're building AI-powered matching and personalized care navigation that help patients get into — and stay in — mental health care at scale. One million patients a month ask for a referral to a mental health provider. We're building the systems that ensure they actually get there.

For Providers

Therapists spend a staggering amount of time on administrative tasks — credentialing, documentation, scheduling, billing — instead of with their patients. We're using AI to automate clinical workflows, simplify complex insurance requirements, and give providers more time to do what they came here to do. The goal: a thriving practice on Headway that practically runs itself.

For Payers

Health insurers are asking harder questions: Is care on Headway actually working? Is it worth what we're paying? We're using AI to answer them at scale — measuring clinical outcomes, building dashboards that demonstrate responsible care, and moving toward a model where patients are matched to the right care pathways and providers are aligned around better outcomes. This work protects Headway's standing with insurers and opens doors to deeper, more strategic partnerships.

For Platform

The infrastructure underneath Headway — billing, claims, payments, and trust and safety — needs to scale reliably at the speed of our growth. We’re using AI to automate complex, high-volume workflows, detect fraud and errors faster, and build systems that get smarter over time. This is foundational infrastructure with direct impact on Headway's economics and compliance posture.

What You'll Do at Headway

• Define and own the product strategy for your area in partnership with engineering, design, data, clinical, and operations teams
• Apply AI where it matters: identify where intelligence creates step-change improvements in your product area and drive those bets from insight through production
• Set and own clear success metrics; communicate results and course-correct with urgency
• Represent the voice of your customer — patient, provider, or health plan — with conviction in every decision, grounded in data and direct research

You'd Be a Great Fit If…

• You have 8+ years of product management experience with a track record of owning complex, high-impact product areas
• You have experience with LLM systems — prompting, retrieval, evaluation, fine-tuning — and a track record of shipping AI-powered products that hold up at scale, not demos.
• You've built at scale in a marketplace, platform, or data-intensive environment — and can show the outcomes you drove
• You're energized by working in regulated, complex industries and see constraints as a product design challenge rather than a blocker
• You can influence across engineering, clinical, legal, finance, and operations — and you're equally comfortable in the data and in the room
• You have strong quantitative fluency and can partner with data scientists on experiment design and causal analysis
• You communicate with precision — in writing, in product reviews, and with senior leadership

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

#LI-EM1

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

Nanonets Health is the healthcare vertical of Nanonets, a global leader in intelligent document processing and AI-driven workflow automation. While Nanonets powers automation across multiple industries, Nanonets Health is purpose-built for Revenue Cycle Management (RCM) and is designed to help providers eliminate the manual, error-prone administrative work that slows down care and reimbursement.

Our platform deploys AI agents across the entire RCM lifecycle:

1. Front-end: patient intake, registration, eligibility, benefits verification, scheduling
2. Payer communication: prior authorizations, claims creation, claims status, documentation requests
3. Back-end: charge capture, posting, payments, collections, denials, appeals

We do this by combining three proprietary technologies inside a unified AI agentic system:

1. Vision-Language Transformers for document-heavy workflows
2. Voice AI Agents for payer calls, patient calls, and follow-ups
3. Browser Automation Agents for system-to-system execution inside EHRs, portals, and payer sites

What once took hours of human effort now takes seconds with Nanonets. Today, 100s of providers rely on us to accelerate & automate admissions, eligibility, coding, claims, and overall revenue performance. 

In 2024, we raised a $29M Series B led by Accel with continued backing from Elevation Capital and YCombinator, fueling our mission to reshape entire industries through intelligent automation. With revenues tripling year over year and a rapidly scaling global team, we’re not just imagining the future of work — we’re building it.

Read about the release here:

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The Role

Nanonets is seeking motivated and results-driven Sales Development Representatives (SDR) to join us. 

We’re looking for SDRs who are not only strong at traditional SaaS outbound (e.g., emails, calls, social) but are also comfortable with in-person, on-site outbound experiments across the U.S. You’ll engage multiple micro-ICPs across healthcare - each with different workflows, incentives, pain points, and buying behavior.

This is not a desk-only SDR role. You will periodically travel for field outreach, on-site prospecting, and industry events aligned with our GTM strategy.

As a SDR at Nanonets, you will play a crucial role in driving our sales pipeline. This position focuses on generating new business opportunities through outbound prospecting. You will engage with potential clients, qualify leads, and set appointments for our sales team. Your efforts will directly contribute to the growth and success of Nanonets. 

Roles and Responsibilities 

• Outbound Prospecting:
• Research and identify potential clients multiple micro-ICP groups across healthcare specialties using various tools and platforms.
• Develop tailored outreach sequences for each ICP, recognizing that pain points differ by specialty, RCM workflows differ across value chain (eligibility, coding, auth, claims, denials) & decision-makers may have different priorities (Practice Admin vs RCM Director vs COO vs Provider-owner)
• Execute multi-channel outbound sequence: email, phone, social, video, physical mailers, and front-desk drop-offs. 
• Travel to cities across the USA where Nanonets is running targeted campaigns.
• Develop and maintain a list of targeted accounts to engage with consistently.
• Conduct discovery calls with prospective accounts to determine fit and schedule follow-up demos for Account Executives.
• Work with the Head of Sales, Head of Account Management, and Head of GTM  to identify ongoing strategic targets.
• Maintain clean CRM notes and insights on each ICP, region, and specialty. 
• Leverage tools(such as LinkedIn Sales Navigator, Apollo) to identify prospective customers.
• Collaboration and Reporting:
• Work with Sales, GTM, and Partnerships on geography-based campaigns and outbound experiments
• Track and report on key performance metrics, including lead conversion rates and pipeline growth.
• Continuously provide feedback on lead quality and market trends to improve outreach strategies.
• Knowledge Development:
• Develop a deep understanding of each micro-ICP, including typical RCM workflow, staffing structures, key pain points in eligibility, auth, coding, claims, and denials etc.
• Stay up-to-date on Nanonets’ products, industry trends, and competitor offerings.
• Attend training sessions and workshops to enhance sales skills and product knowledge.

Requirements and Skills 

• Bachelor’s degree in Business, Marketing, or a related field or equivalent experience.
• 2+ years of experience in sales development, lead generation, or a related role. (healthcare-preferred)
• Excellent communication and interpersonal skills, with a knack for building relationships.
• High ownership mindset with targeted focus on experimentation, iteration, and direct customer interaction
• Strong organizational skills and the ability to manage multiple priorities.
• Familiarity with CRM software and sales engagement tools.
• A self-starter attitude with a passion for technology and automation.

Nice to Have 

• Experience working across multiple healthcare specialties
• Familiarity with workflow automation, RCM operations, or document-heavy processes
• Familiarity with other AI-driven automation, document processing, or healthcare technology platforms.

Additional Information 

Hybrid role (twice a week in our Bellevue office), based in Seattle/Bellevue, WA. The OTE for this position is estimated $80,000-$100,000 annually plus more based on performance and equity. Your salary will be determined by various factors, including relevant experience, skill set, qualifications, and other business needs.

About the role

Join us to build the measurement and decision engine for patient growth.

As a Staff Data Scientist, Growth, you will be the senior analytical and strategic leader who makes marketing performance legible, credible, and actionable. You will partner closely with Growth Marketing leadership and channel owners across paid, lifecycle, and organic, plus Finance, Product, and Engineering. Your job is to help Headway answer the questions that matter:

• What is truly incremental?
• Where should we invest next?
• What is driving performance shifts?
• How do we scale what works without fooling ourselves?

You will build the frameworks, analyses, and modeling approaches that enable the marketing team to move faster with confidence. This is high-stakes decision support for a growth engine that needs to compound and certainly not a dashboard-only role or “just attribution” role. 

What you will do

• Own incrementality measurement across channels. Design and analyze geo tests, holdouts, lift tests, and quasi-experimental approaches when randomized tests are not feasible. Define clear guardrails, decision rules, and what “good” looks like.
• Build a marketing measurement system that leaders trust. Define canonical metrics (CAC, LTV, payback, conversion, retention, capacity-adjusted ROI), ensure definitions are consistent, and create a clear measurement narrative that aligns Marketing, Finance, and Product.
• Turn ambiguity into a plan. When performance changes, you will diagnose why, quantify contributing drivers, and recommend concrete actions. You will be the person who can say, “Here’s what moved, here’s why we believe it moved, and here’s what we do next.”
• Develop and evolve modeling approaches where they create leverage. Build practical models such as LTV and retention forecasting, cohort value prediction, causal uplift models for lifecycle, and marketing mix modeling when appropriate. Focus on models that survive contact with reality: calibration, backtesting, and decision usefulness.
• Partner with Engineering on the measurement plumbing. Improve event instrumentation, identity resolution assumptions, offline conversion integration, and data quality monitoring so measurement is robust. Advocate for minimal, decision-critical requirements that unlock reliable learning.
• Design learning loops that scale. Create repeatable experimentation and analysis templates for channel and creative testing, including measurement of message by audience by surface. Increase testing velocity without lowering the truth standard.
• Influence strategy, not just reporting. Bring an evidence-based point of view on channel allocation, growth constraints, saturation, diminishing returns, and the tradeoffs between short-term acquisition and long-term retention and care outcomes.
• Uplevel the team. Mentor analysts and data scientists working on growth, set quality standards, and help establish best practices across experimentation, causal inference, and forecasting.

What will make you successful

• 10+ years using data science, analytics, and experimentation to drive decisions in marketing, growth, or marketplace environments (or equivalent scope and demonstrated impact).
• Deep expertise in causal inference and incrementality in real-world marketing systems: you know the failure modes (selection bias, channel cannibalization, platform noise, attribution myths) and how to design around them.
• Strong SQL plus strong proficiency in Python or R, with the ability to build reliable, reusable analytical workflows.
• Practical modeling skill, especially as applied to marketing and growth: cohorting, forecasting, LTV estimation, saturation and diminishing returns, MMM concepts, calibration and monitoring.
• Track record of influencing executive decisions with clear recommendations and measurable outcomes, not just analysis.
• Excellent communication: you can make complex measurement logic understandable and defensible to non-technical partners, and you can call out uncertainty without losing momentum.
• High ownership and strong judgment: you prioritize what changes decisions, you move quickly, and you know when to slow down because the risk is real.
• You are motivated by the mission. Access and affordability in mental healthcare are not abstract problems here.

Nice to have

• Experience with geo experiments, marketplace constraints, or capacity-aware marketing optimization.
• Experience measuring acquisition quality beyond conversion: downstream engagement, retention, clinical matching quality, and unit economics.
• Familiarity with lifecycle marketing measurement (incrementality, uplift, experimentation design for messaging).
• Experience partnering with Finance on budget allocation, payback, and scenario planning.
• Comfort working with imperfect identity, privacy constraints, and evolving attribution ecosystems.

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

At Amperity, we’re an AI-first company helping the world’s leading brands create personalized customer experiences that build loyalty and fuel growth. Our AI-powered Customer Data Cloud,  built on multi-patented technology, enables more than 400 global brands, including Alaska Airlines, Wyndham Hotels & Resorts, and DICK’S Sporting Goods, to turn customer data into a competitive advantage.

We unlock the full value of customer data with simplicity and speed. AI is at the core of our platform and the way we work — from powering advanced identity resolution and predictive analytics to streamlining internal workflows and decision-making. It’s not just a capability; it’s part of our DNA.

Our team thrives on curiosity, collaboration, and transparency, fostering a culture where everyone can contribute, learn, and grow. We welcome talented individuals from diverse backgrounds to help us remove data bottlenecks, accelerate business impact, and push the boundaries of what AI can do for the world’s most innovative companies.

With offices in Seattle, New York City, London, and Melbourne, you’ll join a fast-growing team tackling critical challenges at the intersection of AI, data, and customer experience. Ready to make an impact? Let’s talk.

The Role

As our Marketing Operations Manager, you’ll own the strategy and execution of our marketing infrastructure. You’ll lead the charge in evolving our marketing stack—blending traditional automation with AI to build a scalable foundation—ensuring that every system and workflow is built to support our growth as we scale.

The role will own KPI reporting and full funnel conversion metrics and will report to the Sr Director, GTM Operations. 

Interesting Problems

AI-Driven Campaign Execution & Infrastructure

• Tactical Execution: Architect and own the end-to-end campaign engine, leveraging best-in-class tools to drive high-velocity execution, rigorous A/B testing, and top-of-funnel growth
• Autonomous Workflows: Design and deploy AI-driven agents to automate the "operational tax"—orchestrating seamless audience segmentation, intelligent list management, and real-time data synchronization.
• Dynamic Personalization: Spearhead the use of GenAI to bridge the gap between data and delivery, creating a highly personalized customer journey that drives measurable top-of-funnel health.

Intelligence & Attribution

• Reporting: Build the infrastructure for tracking pipeline influence and opportunity attribution, turning raw data into actionable insights for GTM leadership.
• Lead Lifecycle: Design a scalable lead lifecycle management system that utilizes AI to monitor conversion health and predict funnel performance in real-time.
• Advanced Scoring: Establish a best-in-class scoring engine that bridges the gap between marketing engagement and sales readiness, ensuring the team is always focused on the most promising prospects.

Strategic Operations & Alignment

• Lead Handoff: Own the end-to-end strategy and process for lead orchestration—leveraging tools like LeanData and AI-driven 'Form Concierges' to ensure instant, context-aware handoffs and high-velocity alignment between marketing and sales.
• Cross-Functional Partnership: Orchestrate the AI and automation roadmap in lockstep with Sales and Marketing leadership to ensure our tech stack directly accelerates core business objectives.
• Data Governance: Implement a robust data governance framework that secures privacy compliance and enforces the high-fidelity data standards necessary for sophisticated AI modeling.
• Operational Excellence: Institutionalize governance standards for marketing automation and AI, ensuring the "marketing factory" operates with high precision and meets rigorous internal SLAs.

About You

• 8+ yrs of Marketing, Operations, or Campaign Management in high growth environments
• 2+ years admin experience with Marketo & Salesforce
• Advanced technical stack proficiency across attribution (Marketo, Bizible), ABM (Common Room), routing (LeanData), enrichment (Cognism), database architecture (Databricks, Snowflake) and ETL processes 
• Deep understanding of the Marketo-SFDC sync, including field mapping, sync errors, and how scoring/lifecycle field values flow into Salesforce
• Data-driven strategist with a proven track record of translating complex campaign performance into actionable insights
• Working knowledge of HTML and experience building emails
• Detail-oriented by nature, finding as much satisfaction in high-level process design as you do in the tactical 'final mile' of QA, proofreading, and delivering actionable feedback
• Demonstrated curiosity and commitment to continuous learning, staying current with emergent technologies (e.g., AI) and proactive exploration of how new capabilities can be applied to improve marketing operations.
• B2B SaaS marketing preferred

Location

We have a hybrid work model for employees based in Seattle, WA, and New York, NY, with three days in the office days each week, providing a mix of in-person collaboration and remote flexibility

We will also consider fully remote in CA, CO, FL, GA, IL, MA, MN, NJ, OH, OR, and TX

Compensation

• US: NYC, SF Bay Area, Seattle, the range is $137,000 – $188,000.
• US: All other fully remote locations, the range is $120,000 – $170,000.

Cash Incentives: Cash incentives are also available.

Stock Options:  The opportunity for ownership is an exciting part of Amperity’s total compensation package. Every employee at Amperity receives a new-hire equity grant, commensurate with the scope of their position.

Benefits

We offer all the benefits you'd expect from a great place to work: 100% employee healthcare coverage, transportation subsidies, a comfortable work environment with plenty of snacks, and other employee experience perks like events and activities, both in-person and remote. We also offer self-managed PTO and the flexibility to do your best work in the way that works for you. We provide an inclusive environment where you'll be challenged to find and unlock your full potential, surrounded by a team of world-class people driving for excellence. For more details on our benefits, please see our US Benefits & Perks Guide.

Amperity is proud to be an equal opportunity employer. We do not discriminate on the basis of race, religion, color, national origin, sex (including pregnancy, childbirth, and reproductive health choices), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as someone with a disability, political views or activity, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, consistent with applicable federal, state, and local law.

The Work

Payers & Outcomes at Headway sits at the intersection of ML, clinical quality, and trust. You’re building the intelligent systems that protect the integrity of our network — spotting risk, surfacing quality signals, and giving providers real-time feedback so they can deliver great care. What you could work on:

• Clinical Feedback: Architect the LLM-powered systems that review clinical documentation at scale and deliver helpful, real-time feedback to providers. Turn a traditionally painful audit process into a coaching experience — and scale it across the entire network.
• Detecting Risk in Healthcare Claims: Design the ML/LLM systems that spot patterns of inappropriate billing, over-utilization, and low-quality care across millions of appointments and claims. Translate those signals into clear feedback for providers and transparent reporting for our insurance partners.
• Measuring & Elevating Clinical Quality: Help build the systems that systematically review every prescriber in our network against clinical quality standards — so we can measure, improve, and defend the quality of care Headway delivers. The stakes are real: our most recent launch reviews clinical notes and nudges providers to put a safety plan in place when a patient shows signs of suicidal risk — a system projected to save roughly 1,000 lives a year.
• Patient Needs & Provider Fit: Crack the “one size fits all” problem. Build ML systems that understand how complex a patient’s needs are and match them to providers best suited to help — so every patient gets the right care and every provider operates at their best.
• Trustworthy AI in Healthcare: Champion how Headway evaluates and iterates on AI systems. Build the evaluation frameworks, optimization loops, and observability that keep LLM-powered features reliable and safe in a regulated environment.
• Technical Foundations & Mentorship: Set the technical bar for the Payers & Outcomes group — ~12 engineers today, growing to 30–50 by end of year. Lay the architectural foundations other teams will build on, and raise the whole group’s engineering craft as it scales.

#LI-BM1

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

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, AI-assisted clinical documentation, and payment management.
• Patient & Provider Engagement: Deepen the relationship between patients and their care. Build the interfaces and APIs that power seamless communication, personalized experiences, and tools that keep patients connected to their providers — and providers focused on what matters most.
• The Modern AI-Enabled Clinical System: Help design and build the systems that manage clinical data. Create 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 painful process of insurance credentialing into a sleek, consumer-grade experience. Build products and tooling to get providers in-network and scaling their practice in record time.
• Growing the Network: Own the tools and experiences that expand Headway's reach — from acquiring new providers to empowering existing ones to bring their patients onto the platform. Build the infrastructure that fuels sustainable, high-quality growth.
• Technical foundations: Help the teams see around corners and lay the technical foundations for the future of our product. Build systems, tools, and processes that enable the team to ship innovative products quickly, safely, and reliably.
• Strategic leadership: As a Staff Engineer, you will work with a cross functional leadership team to shape the roadmap and technical strategy for the space.

#LI-BM1

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

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

About This Role

Headway’s patient lifecycle function is a blank canvas. You will be the first dedicated lifecycle leader on the patient side: owning strategy, platform, programs, and team from day one. You will build the owned-channel relationship with every Headway patient from first contact through long-term care, using email, SMS, push, and in-app messaging to help people access and sustain mental health care.

This is a player-coach role. You will build and run campaigns yourself while hiring and developing a small team. You will work directly with Engineering to instrument events and ship notification infrastructure, and with Data Science to bring model-driven personalization to lifecycle at scale.

You Will

• Own the end-to-end patient lifecycle: from welcome and onboarding activation through appointment booking, session retention, and re-engagement.
• Select, implement, and operate our lifecycle stack: Iterable (email/SMS) and Knock (in-app/push) in a HIPAA-compliant architecture built on Freshpaint.
• Design and run a rigorous A/B testing program with incremental holdout measurement — not just click optimization.
• Partner directly with Engineering and Data to instrument events, build trigger logic, and deploy ML-informed segmentation and personalization.
• Build AI-assisted workflows for content generation, segmentation, and optimization. You use these tools yourself, today.
• Hire and develop a lifecycle team of 2–3 specialists in H2 2026.

Who You Are

• You have 5+ years in lifecycle/CRM marketing with hands-on experience in Iterable and/or Braze. You have personally built triggered journeys, not just approved them.
• You are fluent in Knock or eager to go deep on it: you understand the distinction between a CRM and a notification layer.
• You design A/B tests with pre-registered hypotheses and holdout groups. You can explain statistical significance to a non-technical stakeholder.
• You have shipped lifecycle programs in partnership with Engineering: you know what a webhook is, you can review a data schema, and you do not wait for tickets to be completed before thinking about logic.
• You are actively using AI tools in your work today: for content, segmentation, or workflow automation. You have a concrete answer to “what have you built with AI in the last 90 days?”
• You have worked in consumer health, consumer subscription, or a context where the user’s emotional journey matters. You understand what it means to send a message to someone managing their mental health.
• You are comfortable with HIPAA compliance considerations in marketing communications — or eager to get up to speed quickly.

Tools We Use

Iterable (evaluating), Knock (evaluating), Freshpaint, RudderStack, Snowflake, Statsig, LaunchDarkly, Braze (considering), Hightouch.

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 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

About The Role

You will be the first dedicated AI Product Manager on the Patient side at Headway. Your mission: build AI-powered products that help patients find the right therapist, stay engaged in care, and achieve measurable improvements in their mental health.  This is not an AI-strategy-deck role. You will ship. You will write evals. You will debug prompt chains. You will partner with ML engineers and data scientists to build products that work for real patients in a HIPAA-compliant environment.  We power over 500,000 appointments per month. Now we are building AI-powered experiences to help patients find the right care and stay in it!

What you’ll do at Headway:

• Own AI-powered patient intake and therapist matching: design LLM-driven flows that understand patient needs and recommend the right provider.
• Build between-session AI support experiences: personalized tools that help patients reflect, prepare, and build therapeutic habits.
• Establish evaluation and safety infrastructure: write evals, build test suites, design red-teaming protocols, and implement human-in-the-loop escalation.
• Advance outcome measurement: move beyond PHQ-9/GAD-7 to AI-informed measurement.
• Partner with Engineering, ML, Data Science, Clinical, and Legal to ship AI products in a HIPAA-compliant architecture.

You’ll be great for this role if you:

• 8+ years of PM experience, with at least 2 years shipping AI/ML-powered products to real customers.
• You have personally written evals for AI product quality.
• You have built multi-step LLM-powered user flows in production.
• Strong technical fluency with LLMs: model selection, RAG architectures, fine-tuning, cost/latency/quality.
• You are a builder who has shipped AI products in partnership with ML engineers.
• Bonus: Experience in regulated industries (healthcare, fintech, insurance).
• Bonus: Experience in healthcare or mental health.
• You understand that building AI for people managing their mental health requires a different level of care and safety.

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

#LI-EM1

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

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

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

About the Role:

We’re looking for a strategic, data-driven, and people-minded leader to own and scale our Owned Channels engine. As the Provider Growth Marketing Senior Manager, Owned Channels, you’ll lead your function across a variety of home-grown, high-intent acquisition channels including Outbound, Referrals, Affiliates, Co-Marketing, Partnerships, and more. You’ll play a key role in shaping how we acquire mental health providers at scale, partnering closely with company leadership, Strategic Finance, Sales, Product, and cross-functional marketing teams to accomplish our ambitious goals.

This role is ideal for a leader who can think big about long-term growth, but also dive into the details of execution, experimentation, and operational rigor. You’ve built or scaled outbound motions before, thrive in cross-functional environments, and know how to unlock new channels with speed and precision. Bonus points if you’ve supported new product launches or worked in product-led growth environments.

You Will:

Own Strategy & Execution Across All Owned Acquisition Channels

• Lead our Owned Channels function including Outbound, Referrals, Affiliates, Co-Marketing, Partnerships, and more to drive efficient provider acquisition
• Shape long-term channel strategy, set quarterly performance goals, and own execution to meet (and exceed) acquisition targets
• Build, refine, and scale processes that turn creative concepts, targeting strategies, and operational insights into predictable pipeline

Build and Evolve Outbound Engines

• Oversee and level up our outbound motion feeding 150+ reps, improving targeting, messaging, cadences, and lead quality
• Partner closely with Sales leadership to ensure channel-to-team alignment and seamless handoff processes
• Introduce new outbound methodologies, tooling, and experimentation frameworks to unlock incremental volume

Unlock Growth Through Data & Forecasting

• Partner deeply with Strategic Finance and Analytics to define KPIs, build forecasting models, and align on investment frameworks
• Translate complex performance trends into clear decisions, prioritizing initiatives based on impact and resourcing
• Develop insights that improve targeting, sequencing, messaging, and channel-level efficiency

Lead, Mentor, and Grow a High-Performing Team of x-y reports

• Foster a culture of accountability, clarity, experimentation, and impact
• Provide coaching, development paths, and day-to-day support while empowering the team to own their respective channels
• Operate both strategically and tactically; comfortable rolling up your sleeves when needed, especially during times of high growth or change

You'd be a great fit if:

• 8–10+ years of experience in growth and acquisition across owned channels, ideally with significant ownership of outbound, partner, or referral channels as well as large budgets
• Experience leading teams and building functions, including hiring, mentoring, and establishing scalable processes.
• Proven track record of scaling owned or partner-driven acquisition channels with measurable business impact
• Strong analytical skills; comfortable working with data teams, forecasting performance, evaluating LOE/LOI tradeoffs, and making ROI-informed decisions
• Demonstrated ability to collaborate cross-functionally with Sales, Finance, Product, Engineering, and Leadership
• Experience supporting new product launches, product-led growth motions, or early funnel product experimentation is a major plus
• Hands-on operator with a bias toward action, able to switch seamlessly between strategy, execution, and people leadership

Bonus points if you have:

• Built outbound engines from scratch (tooling, playbooks, segmentation, cadences) and know what great looks like
• Experience running or scaling referral, affiliate, or co-marketing programs
• Exposure to PLG environments or marketing tied closely to product workflows
• Experience in healthcare, B2B SaaS, or marketplaces, especially those with complex considerations and tradeoffs

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

About this role

Providers are at the heart of Headway’s mission, and the products they use every day play a critical role in both the quality of care patients receive and providers’ ability to sustainably run their practices. Our Provider Experience products are designed to reduce administrative burden, support clinical best practices, and create a seamless care journey for patients — from scheduling and sessions to assessments and follow-up. 

As a Senior Product Manager on the Client Engagement team, you’ll help shape the tools therapists rely on to deliver care, measure progress, and build trusted relationships with their patients, so they can spend less time on operations and more time focused on care. As we grow, we’re looking to build tools that leverage the power of AI and support the end-to-end experience of care between patient and provider, including scheduling, telehealth, in-session tools, and post-session communication, with a focus on reliability and usability.

What you’ll do at Headway

• Own problem discovery, solution design, and delivery for meaningful provider and patient workflows within the Headway platform.
• Translate user needs, business goals, and clinical or compliance considerations into clear product strategy, roadmaps, and execution plans.
• Partner closely with engineering, design, data, clinical operations, and compliance to ship high-quality, high-impact product experiences.
• Stay deeply connected to providers’ and patients’ day-to-day workflows through research, feedback, and data — and use those insights to inform priorities and tradeoffs.
• Integrating AI-powered note-taking into telehealth workflows to reduce documentation burden and improve session quality.
• Exploring agentic AI solutions to streamline provider scheduling and optimize operational efficiency.
• Leveraging AI to surface the full patient journey, enabling providers to build informed treatment plans, prepare for sessions, and deliver more coordinated care.
• Advocate for simple, intuitive experiences that balance usability, operational realities, and regulatory requirements.

You’d be a great fit if…

• You have 5+ years of product management experience, building and shipping user-centric products with complex workflows.
• You’re comfortable operating end-to-end — from discovery and strategy through execution and iteration.
• You’re data-informed and know how to use qualitative and quantitative insights together to drive decisions.
• You bring strong product judgment and UX sensibility, and care deeply about building experiences users trust and enjoy.
• You thrive in ambiguous, fast-paced environments and can bring clarity and momentum to your work.
• You’re a strong cross-functional partner who communicates clearly, builds alignment, and drives progress without formal authority.
• Nice to have: experience in healthcare, clinical tooling, telehealth, assessments, or workflow-heavy B2B or consumer products.

Compensation & Benefits:

The expected base pay range for this position is $185,000 - $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 performance-based variable compensation and 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 Winter Break during the weeks between December 24th and January 1st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

#LI-EM1

About Data Engineering at Headway 

Headway is looking for a Staff Data Engineer to help us get closer to executing our mission: to create access to affordable, quality mental healthcare across the United States. 

The Data Engineering Team is the foundational engine of our data-driven organization. We are a high-impact group of engineers focused on delivering reliable, high-quality data assets at enterprise scale. Our work is centered on transforming raw data into business-ready intelligence through robust ETL/ELT pipelines, advanced data modeling, and rigorous data quality frameworks. We operate with a strong engineering discipline, partnering closely with Data Scientists, Analysts, and core Software Engineering teams to ensure data is not just available, but completely trustworthy for every critical decision and product feature.

About this role

As a Staff Data Engineer, you will be a hands-on technical leader, architect, and mentor, responsible for defining the future state of our data infrastructure. This role focuses on setting architectural direction, establishing organization-wide data standards, and driving the design of highly scalable and optimized data models. You will lead complex, multi-functional initiatives, focusing on data quality governance and the maturity of our pipelines. You will be expected to influence our technology choices, mentor other engineers, and act as the primary technical interface between the Data Engineering team and senior stakeholders across the business.

You Will Love This Role If You Have: 

• 9+ years of experience in data engineering, with a proven track record of architecting and shipping progressively more complex, large-scale data products.
• Expert-level proficiency in our modern data stack, including Snowflake, dbt, Apache Airflow, and Python. You are capable of defining best practices and architectural patterns across these tools.
• Deep mastery of advanced data modeling techniques and their application within production systems to achieve high performance.
• Architectural Ownership: Proven ability to define the technical roadmap for the entire data platform, working horizontally to influence architectural decisions and technical debt management across multiple engineering teams.
• Engineering Elevation: A strong track record of mentoring, coaching, and elevating the technical skills, code quality, and engineering maturity of other data engineers.
• 2+ years of Marketplace Experience: Prior experience in the marketplace or two-sided platform is a significant plus.

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

Join us to build the truth engine behind better mental health outcomes.

As a Senior Staff Data Scientist, Bayesian Experimentation and Causal Inference, you will be the company-wide owner of how Headway learns from data, especially when the stakes are high and the signal is noisy. You will report directly to the Head of Data and serve as a core leader for standards, frameworks, and decision quality across Product, Growth, Ops, and Finance.

Your work will set the default methods for how we answer questions like:

• Did this actually cause the outcome we care about?
• How sure are we, and what should we do given that uncertainty?
• What evidence is strong enough to change strategy, policies, or spend?

A major objective of this role is to build and institutionalize a clear map of “what we know” about patients, providers, and payers, with explicit confidence levels that tie directly to business action. Think of it as a shared language that prevents the organization from treating a correlation like a law of physics, while still moving fast.

What you will do

• Own causal inference and experimentation standards across Headway. Define the canonical approaches, guardrails, documentation, and review mechanisms for experiments and quasi-experiments, including when and how to use Bayesian methods.
• Build the confidence ladder for company knowledge. Create a clear, shared framework that maps findings to levels of confidence (for example 1–10), where lower levels reflect correlation and early directional evidence, mid levels reflect increasingly credible causal inference, and the highest levels reflect stable, repeatable, decision-grade truths. Operationalize it so it shows up in artifacts teams actually use: PRDs, launch reviews, growth planning, quarterly business reviews, and postmortems.
• Design the learning strategy for our hardest questions. Lead the approach for ambiguous, high impact domains like provider activation and retention, payer economics and policies, patient conversion and engagement, and marketplace dynamics. Recommend the right combination of randomized experiments, stepped rollouts, geo tests, natural experiments, and observational designs.
• Raise the organization’s statistical maturity. Introduce and standardize Bayesian experimentation practices where it improves speed and decision quality (priors, posterior interpretation, sequential decision rules, credible intervals, expected value framing). Build training, playbooks, and reusable tooling.
• Be the escalation point for difficult measurement problems. Tackle issues like interference and spillovers, network effects, selection bias, noncompliance, measurement error, multiple comparisons, seasonality, and Simpson’s paradox showing up in real life and causing confusion.
• Partner with Data Platform and Engineering to make rigor scalable. Ensure experimentation and inference are supported by instrumentation, logging, metric definitions, semantic layers, and monitoring. Help define the minimal foundations required for trustworthy learning.
• Build a culture of clear claims. Establish norms for separating facts, estimates, assumptions, and uncertainties. Make it easy for teams to say “we do not know yet” without losing momentum, and easy for leaders to understand what is safe to act on.
• Mentor and set the bar. Coach other data scientists and analytics leaders. Create review standards for causal work, support hiring for methodological depth, and represent Headway’s measurement philosophy internally and externally when appropriate.

What will make you successful

• 12+ years of experience applying causal inference, experimentation, and advanced statistics to real-world product, growth, or operational decisions (or equivalent depth demonstrated through scope and outcomes).
• Deep expertise in causal inference across randomized and observational settings, including practical strategy for when clean experiments are not possible.
• Deep expertise in Bayesian methods for experimentation and decision-making, and strong judgment about when Bayesian approaches outperform frequentist defaults and when they do not.
• Strong SQL and strong proficiency in Python or R, including building reusable analysis tools and improving team workflows.
• Track record of setting org-wide standards that materially improved decision quality and execution velocity.
• Executive-level communication and influence: you can drive alignment across Product, Growth, Ops, Finance, and Engineering.
• Comfort operating in ambiguity, and the ability to turn it into crisp frameworks, clear recommendations, and measurable outcomes.
• Motivation for our mission: improving access and affordability in mental healthcare.

Nice to have

• Experience in marketplaces, healthcare, insurance, or other regulated and complex incentive systems.
• Experience with experimentation under interference and network effects.
• Experience building experimentation platforms, analysis libraries, or statistical tooling used broadly across an organization.
• Familiarity with causal graphs, uplift modeling, and decision theory framing (expected value, value of information).

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

#LI-MG1

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 

1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. 

Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.

We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

About the role

The Trust team at Headway is focused on security and privacy for all of Headway’s customers - therapists, patients, and payers (ex: insurance companies and health systems). As an early member on the team, you’ll have the unique opportunity to be the builder and driver of our dedicated, in-house product and application security engineering efforts. In this role, you will partner closely with our product and engineering teams to ensure that our application is designed and developed securely so that we can maintain and grow customers’ trust in Headway. 

What you’ll do at Headway:

• Partner with Product and Engineering: Headway has many new product launches on the horizon that will transform the industry and have a rich data component. You will be a partner at both the design and development stage to ensure that we implement new features securely, including (but not limited to): 
• Participating in the implementation efforts
• Doing security reviews
• Helping with product design decisions
• Auditing and surfacing vulnerabilities in our current products 
• Develop and Improve our Automated Tooling: Further enhance our automated tooling to scale our application security capabilities and find potential code problems both before and after we deploy.
• Make the safe way, the easy way: Work on defining and building application guardrails so that developers can build securely by default. You also will work to instill a culture of secure development across engineering. 
• Assist in ongoing security operations: You will be part of the security and privacy team and have responsibilities to assist in incident response, vulnerability management, penetration testing, security reviews, and other operational tasks to ensure that our security program is operating at a world-class level.

Tools we use:

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

You’ll be great for this role if you have:

• Have 0 → 1 security experience: You have 5+ years experience in security and/or software engineering roles with a demonstrated history of working on security-related projects or with responsibilities as a security generalist.
• Strong cross-functional experience: You love partnering with other teams to help both teams achieve their goals.
• Strong technical depth and breadth: You have technical experience with building secure platforms and products at a deep level. You are excited to perform security design and code reviews. You want to understand security systems and improve their efficiency and scalability. 
• Thrive in ambiguity: You love tackling ambiguous problems in a fast-paced environment with an optimistic and energizing attitude.
• Innovation at Scale: You seek opportunities to lead the industry in implementing the latest security and privacy technologies.
• Results driven: You care deeply about creating impact and driving results for Headway’s business.
• Mission driven: You are motivated by Headway’s mission, increasing access to high quality mental health care.

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 a member of our Security Engineering team for introductions and an architecture interview. Conducted similarly to a System Design interview, we’ll learn more about your knowledge of the role of security in engineering systems and web architecture.  
• Final rounds: You’ll meet several more team members for technical and non-technical interviews, including our CISO who this role reports to, 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:

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

#LI-SC1

About the role

Join us to build the decision engine for better mental health outcomes.

As a Staff Data Scientist, Product Analytics, you will be a senior technical and strategic leader for how Headway measures, learns, and improves. You will own the hardest and most ambiguous product questions, shape how we define success, and drive decisions that cut across multiple teams and product surfaces. You will not only run the analyses, you will influence what we build, how we evaluate it, and how we scale what works.

This role is for someone who can zoom in to debug a metric definition and zoom out to design a measurement strategy for a major product area, then bring the organization along with them.

What you will do

Everything in the Senior role, plus:

• Own a product measurement strategy. Define north star and input metrics for a major product area (or multiple surfaces), align stakeholders on definitions, and build conviction in what “good” looks like.
• Lead multi-team initiatives. Drive cross-functional work where the right answer is not obvious and the path is not linear, and ensure we land measurable outcomes.
• Set the experimentation standard. Establish frameworks for test design, guardrails, decision rules, and interpretation that improve both speed and rigor across teams.
• Develop evaluation systems for complex products. For areas like matching, ranking, or applied AI experiences, build measurement approaches that combine offline evaluation, online experiments, and human-quality signals when needed.
• Build scalable analytical assets. Invest in durable measurement systems: semantic definitions, self-serve dashboards, monitoring and alerts, and repeatable templates that reduce ad hoc work.
• Mentor and uplevel. Coach other data scientists and analytics partners, provide strong technical review, and model what great looks like.
• Be a thought leader. Proactively identify opportunities, shape roadmaps with an evidence-based POV, and create clarity where teams feel stuck.

What will make you successful

• 10+ years using data to drive product or business decisions in product, growth, engineering, or operations environments (or equivalent depth of experience and scope).
• Expert fluency in SQL and strong proficiency in Python or R, including building reliable, reusable analysis workflows.
• Deep expertise in Bayesian experimentation, causal inference, and measurement design, including common failure modes and how to prevent them.
• Strong applied modeling judgment: you know when a model is the right tool, and you can build, validate, and launch responsibly.
• A track record of leading ambiguous, cross-team work and delivering measurable outcomes (not just insights).
• Excellent executive communication and influence: you earn trust, align stakeholders, and move decisions forward.
• Strong product sense and an instinct for decision leverage: you focus on what changes outcomes, not what is merely interesting.
• Motivation for our mission: improving access and affordability in mental healthcare.

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

#LI-MG1

About the Data Engineering Team

Headway is looking for a Senior Data Engineer to help bring us closer to our mission: creating access to affordable, quality mental healthcare across the United States.

Data is foundational to that mission. It powers everything from critical business decisions to the systems that support patients, providers, payers, and internal teams. The Data Engineering team builds and maintains the infrastructure that makes this possible. We partner closely with stakeholders across the company - including Finance, Insurance Systems, Analytics, Product, and Data Science - to ensure that Headway's data platform is scalable, reliable, and secure.

As a Senior Data Engineer, you'll help shape the future of our data architecture. You’ll work cross-functionally to design and implement robust data pipelines, define and uphold data governance standards, and ensure our platform is built to meet the growing needs of the business.

In this role, you will:

• Design, build, and maintain scalable data pipelines and infrastructure to support internal stakeholders and core business functions
• Define, develop, and refine data governance, monitoring, and quality standards across the company
• Partner with Product and Engineering to advocate for best practices in data engineering and ensure data needs are addressed early in the product lifecycle
• Work cross-functionally with Analytics, Data Science, and Infrastructure to continuously evolve Headway’s data architecture
• Own and drive technical decisions across the data platform, contributing to everything from performance optimization to infrastructure-as-code

You will love this role if you have:

• 6+ years of experience as a data engineer, with a track record of building scalable systems and solving complex data problems in a fast-paced tech environment
• Proficiency in Python and SQL
• Experience with tools and services that encompass a modern data platform stack, such as Snowflake, dbt, Airflow, Fivetran, and Terraform
• Familiarity with visualization tools like Metabase or Jupyter Notebooks is a plus!
• A pragmatic approach to building for both today’s needs and tomorrow’s scale
• A strong sense of ownership and a bias toward action, especially in the face of ambiguity
• Empathy for your teammates and stakeholders, and a collaborative mindset that values working across disciplines
• Passion for Headway’s mission to make mental healthcare more accessible and affordable

Compensation and Benefits:

The expected base pay range for this position is $180,000 - $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

About the role:

We're seeking a Senior Product Manager to lead our Provider Acquisition pod. Your mission will be to drive sustainable user acquisition and revenue growth through data-driven search marketing strategies and product optimizations. You'll partner with Engineering, Marketing, Data, and Design to build scalable growth systems that maximize our search visibility and conversion funnel performance. The ideal candidate thrives in a metrics-driven environment, has expertise in search marketing, and is passionate about leveraging product innovation to accelerate growth.

What you’ll do at Headway:

• Develop and execute a comprehensive growth strategy that leverages SEO, SEM, and product to drive provider acquisition, engagement, and retention.
• Partner with engineering and data science teams to implement features, landing pages, and experiences that improve our ability to find and acquire new providers across multiple segments 
• Collaborate with content and marketing teams to align SEO content strategy with product roadmap and business objectives.
• Design, launch, and optimize referral programs, invite flows, and affiliate networks to accelerate acquisition

You’ll be great for this role if you:

• Bring growth experience: You have 5+ years of product management experience with demonstrated success in growth-focused roles, ideally with SEO and SEM expertise, and the proven ability to drive measurable results.
• Are data and results driven: You love running experiments and are a master at digging into data, defining clear goals, running toward them & bringing your team along the way.
• Are highly collaborative: You work well with other functions and teams and can collaborate on delivering impact together to a shared goal. 
• Thrive in ambiguity: You love tackling ambiguous problems in a fast-paced environment with an optimistic and energizing attitude.

Compensation and Benefits:

The expected base pay range for this position is $180,000 - $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-EM1