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

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 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

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

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