Staff Software Engineer (Payer)

Salary: $264,000 - 330,000 per year Requirements:

• Were looking for a senior engineer who can build end-to-end products, balancing API design with polished user experiences.
• We value someone who has driven ambiguous initiatives from concept to shipped software and can align the right stakeholders when priorities change.
• You should make technical choices that favor long-term maintainability and scalability, not just speed to launch.
• We want a natural mentor who brings others into design conversations and strengthens the team through thoughtful code reviews and knowledge sharing.
• You should move quickly from problem framing to a workable solution, while iterating based on real feedback.
• We need someone who can learn complex, unfamiliar domains quickly; prior healthcare experience is not required.
• You should be motivated by meaningful impact and eager to help improve mental healthcare access.
• We expect clear, concise communication across written and live collaboration settings.
• You should actively explore AI tools and LLM-based workflows, with a practical mindset for building responsibly in healthcare.
• Experience with our stack is helpful, including TypeScript, Python, React, Remix, Next.js, FastAPI, SQLAlchemy, Postgres, Redis, Snowflake, AWS, Temporal, Kafka, Datadog, Sentry, and PagerDuty.

• Build intelligent systems that safeguard the quality and trustworthiness of our network.
• Design and ship LLM-powered workflows that review clinical documentation and provide timely feedback to providers.
• Create ML and AI solutions that identify risky billing, overuse, and care-quality issues across claims and appointments.
• Help develop systems that evaluate prescribers against clinical quality standards and support safer patient care.
• Build matching models that better connect patients with providers suited to their needs.
• Establish evaluation, observability, and optimization frameworks that keep our AI features reliable and safe in a regulated setting.
• Set the technical direction for the Payers & Outcomes engineering group as it grows, laying foundations other teams can build on.
• Mentor engineers and help raise the overall engineering standard across the team.

• AI
• API
• AWS
• Datadog
• FastAPI
• Support
• Kafka
• LLM
• Network
• PagerDuty
• Python
• React
• Redis
• Sentry
• Snowflake
• Spark
• TypeScript
• Cloud
• Architect
• Backend
• Cursor
• Frontend
• Slack

More:

We are Headway, and our mission is to make mental healthcare accessible by fixing the insurance and administrative barriers that keep therapy out of reach. Our platform is used by more than 75,000 providers across all 50 states and supports over 1 million patients. We are a Series D company backed by investors including a16z, Accel, and Spark Capital. This staff engineering role is based in one of our three hubs: NYC, San Francisco, or Seattle. There is no onsite requirement, and engineers may work from these regions while also having access to offices in those cities. We offer a competitive base salary of $264,000 to $330,000 plus equity, comprehensive medical, dental, vision, HSA/FSA, 401(k), fertility support, parental leave, therapy reimbursement, professional development funding, and generous time off.

last updated 33 week of 2026