Staff Product Manager, AI Patient Experience

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare 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. ABOUT THE ROLE You will be the first dedicated AI Product Manager on the Patient side at Headway. Your mission: 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! 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 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.

• Benefits offered include: - 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 #LI-EM1 We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience.

• Highlight any experience building AI‑driven product features in regulated healthcare settings (e.g., HIPAA‑compliant recommendation engines, clinical decision support). Include metrics such as reduced claim‑processing time or improved patient‑match accuracy, and be ready to discuss how you navigated privacy and compliance constraints.
• Prepare a short “product deep‑dive” case study (2‑3 slides) that walks through the end‑to‑end lifecycle of an AI feature you launched: problem framing, data pipeline design, model selection, integration with existing billing/credentialing systems, and post‑launch impact. Bring this to the interview and reference it when answering product‑strategy questions.
• Demonstrate mastery of the core tooling Headway uses: JIRA/Confluence for agile workflow, Mixpanel or Amplitude for product analytics, and Figma for collaborative design hand‑offs. Mention any scripts or dashboards you built (e.g., Python/SQL for monitoring AI model drift) and how they informed roadmap decisions.
• Show you understand Headway’s mission‑first mindset by sharing a concrete idea for improving the “therapist‑patient matching” experience with AI—outline the hypothesis, required data sources (insurance eligibility, therapist specialization, patient preferences), and a quick experiment plan (A/B test, success metrics, risk mitigation). This signals you can think strategically about scaling mental‑health access.
• When discussing compensation, research remote senior PM benchmarks for health‑tech AI roles (e.g., $170‑200k base + 0.2‑0.3% equity). Prepare a concise value‑proposal sheet tying your prior outcomes (e.g., $X million in saved admin costs) to the impact you’ll bring at Headway, and be ready to negotiate a total‑comp package that reflects both base salary and equity upside.