Staff Software Engineer (Payer)

Headway•San Francisco, NY

About The Position

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 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 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 therapists 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, React, Remix, Next.js, React Aria Infrastructure: AWS (Fargate, ECS, S3, and more), Spark and Kafka Monitoring: Datadog, PagerDuty, Sentry Version Control: Github, PagerDuty Projects we’re working on: At Headway, we treat infrastructure and developer experience as force multipliers. Our teams work on high-leverage problems at the intersection of scale, healthcare complexity, and real-world impact—often without the safety net of large, fully staffed orgs. What makes this work unique is that, as the largest provider network in the U.S., we have a rare opportunity to prove to the market that this model can work—and that it meaningfully improves care. Our Payers and Outcomes group is making early, foundational architecture decisions that will shape how Headway scales and how we integrate with payers and measure outcomes over the long term. We’re building the technology that allows us not just to identify risk, but to actively support providers in doing better work—starting with operational areas like coding and billing, and extending into much more nuanced clinical practice. In partnership with top clinicians, we are developing applied LLM systems that can deliver actionable, trustworthy feedback to providers: helping them improve documentation, reduce administrative burden, and ultimately raise the level of care toward more evidence-based and value-based practice. This requires balancing automation with explainability and trust in a highly regulated environment. At the same time, we are tackling the “one-size-fits-none” problem in mental healthcare. We recognize that providers have different strengths and areas of excellence, and we are building systems that match patient acuity to those strengths—so patients receive the right level of care and providers can operate at the top of their license. There is still much to do. But this work represents a true paradigm shift for mental healthcare in the U.S.—a generational change in how quality, outcomes, and access are aligned. This is the technology we are building, and this is the impact we are here to drive. These initiatives reflect how we operate: small teams, high ownership, technically deep problems, and outcomes that matter—to the business, providers, and patients alike.

Requirements

You have experience working across the stack on modern web applications
Strong understanding of at least one programming language and comfortability with others
Shaped work to achieve company and team goals
Flexed into new technical and non-technical areas as projects require
Committed team member supporting the growth of those around them
Has designed and scaled ML / LLM-powered systems in production
Architected complex systems spanning multiple technical domains or product areas (e.g., publishing npm packages or owning infrastructure depended on by multiple teams)
Driven technical vision and strategy at the organization level, by writing and reviewing technical design documents and participating in quarterly planning activities
Established engineering standards and best practices across multiple teams
Led major technical initiatives requiring coordination across multiple teams
Mentored senior engineers and technical leaders

Benefits

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