Job Description
1 in 4 people in the US have a treatable mental health condition but most providers don't accept insurance making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing claims payment reconciliation - is a nightmare. We've automated that.
But we're going further. Over 75000 providers across all 50 states run their practice on our software serving over 1 million patients. We are building the best tools for therapists to run their entire practice reimagining the experience of finding a therapist and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.
We're a Series D company with $325M+ in funding (a16z Accel Spark Capital etc.) looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us and help change mental healthcare for the better.
The Revenue Engine Team is making the foundational platform decisions that will shape how Headway moves money — between patients providers and payers — at the scale our growing network demands. As one of two staff engineers in the group you'll partner with engineering leadership to set technical direction across our Payment Platform and Clearinghouse Platform teams: the systems responsible for our integrations with Stripe Plaid and the payer clearinghouses that our claims flow through.
This is platform work in the truest sense. Every payment that's charged or paid out every claim that's filed and reconciled every dollar that flows through Headway depends on the systems your teams own. As Headway's network grows — more patients more providers more payers more transaction volume — the reliability throughput and correctness of these systems become the difference between a business that scales and one that doesn't. Provider trust patient trust audit readiness and revenue capture all hinge on this surface area.
You'll lead the design of fault-tolerant observable and deeply reconciled integrations with the third-party services we depend on. You'll build the abstractions and standards that let dozens of adjacent engineering teams — Billing Infrastructure Patient Billing Provider Payouts and others — ship faster and more safely on top of our platform. And you'll do it as a hands-on technical leader: writing code where leverage is highest mentoring senior engineers across both pods and shaping the operational excellence that this domain demands.
This role is for engineers who get energized by distributed systems problems with real consequences — concurrency idempotency partial failures all with a substantial potential blast radius — and who want to apply that craft to a mission that actually matters: building a mental healthcare system that everyone can access.
- 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)
- 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?
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!
- Salary: $224000 - $280000 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
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.
A notice to Headway applicants: To protect yourself against phishing and recruitment fraud please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites ask for payment or personal information or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel please do not share any information and report it as spam.
Skills Required
- Expertise in TypeScript and Python
- Experience with distributed systems and payments systems
- Strong knowledge of AWS and related technologies
- Ability to mentor and guide other engineers
- Experience with database technologies like Postgres
- Familiarity with modern frontend frameworks
What the Team is Saying




Headway Compensation & Benefits Highlights
- Healthcare Strength—Medical dental and vision plans offer multiple Cigna options with the employer covering a majority of premiums. Mental-health support includes an HRA reimbursing eligible therapy costs up to $2100 per year and access to an EAP.
- Parental & Family Support—Up to 16 weeks of fully paid parental leave is available to eligible full-time employees. Family-forming support is enhanced through a partnership with Carrot Fertility.
- Leave & Time Off Breadth—Flexible/generous PTO is paired with 56 hours of paid sick time and 13 paid holidays. A company year-end holiday break (Dec 25–31) is also noted.
Headway Insights
What We Do
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 60000 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.
Why Work With Us
The demand for mental health care has never been higher underscoring the need for solutions like Headway that increase accessibility to clinical care. 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.
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Headway Offices
Remote Workspace
Employees work remotely.
Headway employees work remotely across the US with the option to work from offices in New York City San Francisco and Seattle.
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Date Posted
06/05/2026
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