Staff Product Manager, AI Patient Experience

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 The Role

You will be the first dedicated AI Product Manager on the Patient side at Headway. Your mission: build AI-powered products that help patients find the right therapist, stay engaged in care, and achieve measurable improvements in their mental health.  This is not an AI-strategy-deck role. You will ship. You will write evals. You will debug prompt chains. You will partner with ML engineers and data scientists to build products that work for real patients in a HIPAA-compliant environment.  We power over 500,000 appointments per month. Now we are building AI-powered experiences to help patients find the right care and stay in it!

You Will:

Own AI-powered patient intake and therapist matching: design LLM-driven flows that understand patient needs and recommend the right provider.

Build between-session AI support experiences: personalized tools that help patients reflect, prepare, and build therapeutic habits.

Establish evaluation and safety infrastructure: write evals, build test suites, design red-teaming protocols, and implement human-in-the-loop escalation.

Advance outcome measurement: move beyond PHQ-9/GAD-7 to AI-informed measurement.

Partner with Engineering, ML, Data Science, Clinical, and Legal to ship AI products in a HIPAA-compliant architecture.

Who You Are:

8+ years of PM experience, with at least 2 years shipping AI/ML-powered products to real customers.

You have personally written evals for AI product quality.

You have built multi-step LLM-powered user flows in production.

Strong technical fluency with LLMs: model selection, RAG architectures, fine-tuning, cost/latency/quality.

You are a builder who has shipped AI products in partnership with ML engineers.

Bonus: Experience in regulated industries (healthcare, fintech, insurance).

Bonus: Experience in healthcare or mental health.

You understand that building AI for people managing their mental health requires a different level of care and safety.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

Equity compensation

Medical, Dental, and Vision coverage