Staff Software Engineer (Journeys)

Remote: yes Posted: 2026-08-10

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 90,000 providers across all 50 states run their practice on our software, serving over 2.6 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, and building much of it with AI. 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.

- We’re looking for a Staff Engineer to be the technical anchor of the Journey team. This is a senior IC role — the person who owns the architecture of how Headway communicates at scale. You’ll design and evolve the decision engine, experimentation layer, and channel orchestration that will define how Headway reaches patients and providers for years to come. You’ll set the technical direction for a multi-vendor communications stack, own the unified message ledger, and bring LLM-powered personalization from concept to production.

- This role is high-leverage and cross-functional. You’ll work closely with marketing, CX, product, and the patient org — and your work will directly impact patient acquisition, retention, and health outcomes.

- We’re looking for experienced engineers who have the ability to deal with ambiguity and learn new technologies and systems. Below are some additional experiences we think help engineers succeed at Headway.

- A systems thinker who holds the architecture of a complex, multi-vendor platform and guides the team through it

- An engineer who has shipped high-throughput, event-driven systems in production and knows what reliability requires