Staff Product Manager

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. 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.

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

Requirements

Curious about what AI makes possible and eager to build in an environment where it's a core part of the toolkit; 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 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

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