Director, Engineering Patient

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.

About Headway

Headway's mission is to build a new mental health care system that everyone can access. We've built technology that takes the hardest parts of mental healthcare finding the right provider, navigating insurance, managing payments — and makes them simple. We're now one of the fastest-growing companies in healthcare, with more than 200,000 patients finding care through Headway and thousands of therapists using our platform to grow their practices.

We believe AI is the unlock for our next phase — more intelligent matching, more personalized patient experiences, and a fundamentally different way of building software. This role sits at the center of that transition.

About Patient Core Experience at Headway

The Patient Core Experience team is building what we believe will become one of the most consequential AI products in healthcare: a system that connects patients with therapists who are genuinely right for them.

Our four engineering pods — Onboarding, Profiles + Checkout, Ranking + Relevance, and Activation — own the full patient journey from first visit through early retention. Today, our matching is largely filter-based. We're rebuilding it as an intelligent system that uses communication style, data-backed expertise signals, patient-reported outcomes, and behavioral signals to surface the right provider for each patient at the moment they're ready to get help.

We operate a three-sided marketplace (patients, providers, payers) with real complexity and massive impact. The leap from directory to intelligent matching platform is the defining technical challenge for this team. It requires both serious AI/ML product work and a leader who has already made the shift to AI-augmented engineering — and has opinions about what that means in practice.