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HeadwayHeadway

Staff Product Manager, AI Patient Experience

First AI PM on the patient side building LLM-powered products for therapist matching, between-session support, and outcome tracking in a HIPAA-compliant environment.

About the job

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

Skills

LLMs, Rag Architectures, Fine-Tuning, Model Selection, Prompt Engineering, Ai Product Evaluation, Multi-Step Llm Flows, Ml Engineering Collaboration, Hipaa Compliance, Outcome Measurement

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