Principal Product Manager

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