# Staff Product Manager, AI Patient Experience

**Company:** [Headway](https://hotfix.jobs/companies/headway)
**Location:** Remote
**Role:** Product Management
**Salary:** $265k – $332k/yr
**Experience:** 8+ years
**Skills:** LLMs, Rag Architectures, Fine-Tuning, Model Selection, Prompt Engineering, Ai Product Evaluation, Multi-Step Llm Flows, Ml Engineering Collaboration, Hipaa Compliance, Outcome Measurement
**Posted:** 2026-06-24

> 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.

## Job Description

## 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

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