Staff Product Manager, AI Patient Experience

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

• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development