Senior / Staff/ Principal Product Manager

About The Role

We're looking for Product Managers across Senior, Staff, and Principal levels who are curious builders, eager to drive company level impact and to build in an environment where AI is a core part of the toolkit.

We are hiring across Patient, Provider, Payer, and Platform. The right candidates will bring strong product fundamentals and a willingness to build with AI in a regulated, high-stakes industry.  Product Managers at Headway own product areas end-to-end: setting strategy, partnering deeply with engineering, data science, and design, and driving outcomes that move the company.

The way we are building is continuously evolving, and the size of opportunity for Headway to leverage AI is massive. We sit at the intersection of healthcare delivery, complex insurance systems, and a multi-sided marketplace serving tens of thousands of providers and millions of patients.

The Problems We're Solving

For Patients

• Finding the right therapist, understanding your insurance benefits, and staying in care shouldn't be hard. Today it is. We're building AI-powered matching and personalized care navigation that help patients get into — and stay in — mental health care at scale. One million patients a month ask for a referral to a mental health provider. We're building the systems that ensure they actually get there.

For Providers

• Therapists spend a staggering amount of time on administrative tasks — credentialing, documentation, scheduling, billing — instead of with their patients. We're using AI to automate clinical workflows, simplify complex insurance requirements, and give providers more time to do what they came here to do. The goal: a thriving practice on Headway that practically runs itself.

For Payers

• Health insurers are asking harder questions: Is care on Headway actually working? Is it worth what we're paying? We're using AI to answer them at scale — measuring clinical outcomes, building dashboards that demonstrate responsible care, and moving toward a model where patients are matched to the right care pathways and providers are aligned around better outcomes. This work protects Headway's standing with insurers and opens doors to deeper, more strategic partnerships.

For Platform

• The infrastructure underneath Headway — billing, claims, payments, and trust and safety — needs to scale reliably at the speed of our growth. We’re using AI to automate complex, high-volume workflows, detect fraud and errors faster, and build systems that get smarter over time. This is foundational infrastructure with direct impact on Headway's economics and compliance posture.

What You'll Do at Headway

• Define and own the product strategy for your area in partnership with engineering, design, data, clinical, and operations teams

• Apply AI where it matters: identify where intelligence creates step-change improvements in your product area and drive those bets from insight through production

• Set and own clear success metrics; communicate results and course-correct with urgency

• Represent the voice of your customer — patient, provider, or health plan — with conviction in every decision, grounded in data and direct research

You'd Be a Great Fit If…

• You have 8+ years of product management experience with a track record of owning complex, high-impact product areas

• You have experience with LLM systems — prompting, retrieval, evaluation, fine-tuning — and a track record of shipping AI-powered products that hold up at scale, not demos.

• You've built at scale in a marketplace, platform, or data-intensive environment — and can show the outcomes you drove

• You're energized by working in regulated, complex industries and see constraints as a product design challenge rather than a blocker

• You can influence across engineering, clinical, legal, finance, and operations — and you're equally comfortable in the data and in the room

• You have strong quantitative fluency and can partner with data scientists on experiment design and causal analysis

• You communicate with precision — in writing, in product reviews, and with senior leadership

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