Principal Product Manager

About the Position

Principal Product Manager

Headway is on a mission to revolutionize mental healthcare by making it accessible and affordable for everyone. We are seeking a Principal Product Manager to join our team and lead some of our highest-stakes, most complex product areas. If you have a builder-mindset, are curious about what AI makes possible, and are eager to build in an environment where AI is a core part of the toolkit, we want to hear from you.

Location

• Remote
• New York City, United States
• San Francisco, CA, United States
• Seattle, WA, United States

Employment Type

Full time

Compensation

• $300K – $375K • Offers Equity

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Responsibilities

As a Principal Product Manager at Headway, 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.

Requirements

• 10+ years of product management experience with a track record of owning large, complex product domains end-to-end.
• Experience in shaping strategy at the org level - not just your team's roadmap, but how multiple teams think about what to build and why.
• Proven track record of building 0→1 and scaling - you've launched something new and also meaningfully improved something that already existed at scale.
• Deeply technical - you can have architectural conversations with engineers, challenge assumptions, and make informed build-vs-buy calls.
• Experience influencing at the executive level - presenting strategy, fielding hard questions, and getting buy-in without formal authority.
• Experience in leveling up PMs around you through mentorship, collaboration, or the quality of your own work.
• Thrive in ambiguity - you define the problem as readily as you solve it.
• 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.
• Motivated by Headway's mission of making mental healthcare accessible and affordable.

We Offer

• Competitive salary range: $300K - $375K
• Equity options
• Comprehensive health and wellness benefits
• Retirement savings plan
• Professional development opportunities

About the Company

Headway is a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.). 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. We aren't just a billing layer; we are becoming the platform where care actually happens.

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.

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.