About the role
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)