Principal Product Manager

About This Role

We're looking for Principal PMs to lead some of our highest-stakes, most complex product areas. Principal Product Managers who have a builder-mindset, and 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're actively hiring across our Patient, Payer, Provider, and Platform Product teams, and we open this pipeline to find exceptional Principal PM talent as the right roles take shape.

As a Principal PM at Headway, you'll own a significant product domain end-to-end — defining the strategy, aligning stakeholders up to and including executive leadership, and setting a high bar for what great product looks like. You'll work with a high degree of autonomy on problems that don't have obvious answers. You'll shape the roadmap from first principles, not execute against one that's handed to you.

This is not a role for someone who needs a well-defined problem. The best candidates have a track record of finding the right problem and convincing the organization to solve it.

The Problems We're SolvingFor 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.

You will..

• Define the strategy for a major product domain. Identify the highest-leverage bets Headway should make, make the case with data and customer insight, and drive alignment across engineering, design, clinical, legal, operations, and executive leadership.
• Ship meaningful product. Not strategy decks — real product with measurable outcomes. You'll own the roadmap end-to-end, navigate tradeoffs under uncertainty, and hold a high bar for quality and velocity.
• Lay foundations that last. Build capabilities, frameworks, or systems that unlock the next 2–3 years of product work across your domain — not just what's needed this quarter.
• Elevate PM craft on your team. As one of the most senior ICs on the PM team, you'll set the standard for what great product thinking looks like — mentoring PMs, raising our hiring bar, and influencing how the broader product org works.
• Drive alignment across complexity. Work across engineering, design, data, clinical, legal, operations, and finance without formal authority — and get the right work resourced, sequenced, and shipped.

You'd Be a Great Fit If

• 10+ years of product management experience with a track record of owning large, complex product domains end-to-end
• You've shaped strategy at the org level — not just your team's roadmap, but how multiple teams think about what to build and why
• You've built 0→1 and scaled — you've launched something new and also meaningfully improved something that already existed at scale
• You're deeply technical — you can have architectural conversations with engineers, challenge assumptions, and make informed build-vs-buy calls
• You've influenced at the executive level — presenting strategy, fielding hard questions, and getting buy-in without formal authority
• You've leveled up PMs around you through mentorship, collaboration, or just the quality of your own work
• You thrive in ambiguity — you define the problem as readily as you solve it
• You're AI-fluent — you understand how to evaluate and deploy AI-powered features responsibly and have a point of view on where AI creates real product leverage
• You're motivated by Headway's mission of making mental healthcare accessible and affordable

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.

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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 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.