Senior Staff Software Engineer (Payer)

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 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. 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 Doma