Staff Product Manager

Headway•San Francisco, NY

1d•Remote

About The Position

We're looking for Staff PMs who are curious about what AI makes possible and eager to build in an environment where it's a core part of the toolkit — not a side project. 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. Staff PMs 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. AI is changing how we build at Headway, 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. AI is increasingly part of how we solve these problems — and we want PMs who are energized by that, whether they're deep in AI already or strong product thinkers ready to learn.

Requirements

8+ years of product management experience with a track record of owning complex, high-impact product areas
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.
Built at scale in a marketplace, platform, or data-intensive environment — and can show the outcomes you drove
Energized by working in regulated, complex industries and see constraints as a product design challenge rather than a blocker
Can influence across engineering, clinical, legal, finance, and operations — and you're equally comfortable in the data and in the room
Strong quantitative fluency and can partner with data scientists on experiment design and causal analysis
Communicate with precision — in writing, in product reviews, and with senior leadership

Responsibilities

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

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