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HeadwayHeadway

Principal Product Manager

Lead high-stakes product domains end-to-end at a Series D mental health platform. Define strategy, ship AI-powered products, and drive alignment across engineering, clinical, and executive teams.

About the job

Responsibilities

  • 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 with measurable outcomes. 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.
  • Elevate PM craft on your team. Mentor PMs, raise hiring bar, and influence how the broader product org works.
  • Drive alignment across complexity. Work across engineering, design, data, clinical, legal, operations, and finance without formal authority.

Requirements

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

Nice-to-Haves

  • Experience in healthcare, insurance, or regulated industries
  • Prior experience with AI/ML product development at scale

Skills

Product Management, Product Strategy, Roadmapping, Stakeholder Management, Ai/Ml Product Development, Data Analysis, Executive Communication, Cross-Functional Collaboration, 0 To 1 Product Development, Mentorship

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