Senior / Staff/ Principal Product Manager

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 90,000 providers across all 50 states run their practice on our software, serving over 2.6 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, and building much of it with AI. 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 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 LI-EM1 COMPREHENSIVE BENEFITS: Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave. 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. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview. Headway participates in E-Verify. To learn more, click here. https://www.e-verify.gov/sites/default/files/everify/posters/EVerifyParticipationPoster.pdf A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com http://findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam. Compensation: $262.2K - $375.5K