Staff Product Manager, AI Patient Experience

Headway
$265,200 - $331,500Remote

About The Position

Headway's mission is to fix the mental healthcare system by building a new system everyone can access, starting by solving the biggest barrier to care: insurance. They have automated the administrative work like credentialing, claims, and payment reconciliation. Over 75,000 providers across all 50 states use their software, serving over 1 million patients. Headway is building the best tools for therapists, reimagining the experience of finding a therapist, and investing in platform foundations to enable scale. They are a Series D company with over $325M in funding and are looking for exceptional people to help achieve their mission. This role is the first dedicated AI Product Manager on the Patient side, focused on building AI-powered products to help patients find the right therapist, stay engaged in care, and achieve measurable improvements in their mental health. The role involves shipping AI products, writing evaluations, debugging prompt chains, and partnering with ML engineers and data scientists in a HIPAA-compliant environment. Headway powers over 500,000 appointments per month and is now building AI-powered experiences to help patients find and stay in care.

Requirements

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

Nice To Haves

  • Experience in regulated industries (healthcare, fintech, insurance).
  • Experience in healthcare or mental health.

Responsibilities

  • 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.

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
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