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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 75,000 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 Work
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.
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?

Location: We are hiring our Staff Engineering roles out of our 3 hubs - NYC, SF, and Seattle. There is no onsite requirement, but engineers should be located in one these regions. There are offices in these 3 cities for anyone interested in in-office time.
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: $264,000 - $330,000 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.