Staff Product Manager, AI Patient Experience

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 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! What you’ll do at Headway: 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. You’ll be great for this role if you: 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. Compensation and Benefits: The expected base pay range for this position is $ 212,000 - $265,000 , based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level. 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 HSA / FSA 401K Work-from-Home Stipend Therapy Reimbursement 16-week parental leave f ... (truncated, view full listing at source)