About the Position

Staff Product Manager, AI Patient Experience

We are looking for a dedicated AI Product Manager to join our team at Headway. Your mission: to 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!

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.

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.
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 Offer

Competitive salary range: $265.2K – $331.5K
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

About the Company

Headway is 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.

Headway’s mission is to fix the mental healthcare system by building a new 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.

Locations

Remote
New York City, United States
San Francisco, United States
Seattle, United States

Employment Type

Full time

Work Location Type

Remote

Staff Product Manager, AI Patient Experience

Job description