Staff Product Manager, Monetization and Pricing

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

You will be the first dedicated PM for pricing at Headway. Your mission: build pricing into a durable, experimentation-driven lever for growth and revenue. Success looks like creating $100M+ of revenue impact.

Headway's pricing decisions affect every participant in our marketplace — what providers earn, what patients pay, and what payers reimburse. Today, these decisions are made through a mix of analysis, intuition, and competitive benchmarks. You'll replace that with a systematic, experiment-driven approach that generates data, builds conviction, and creates new revenue streams through bundling/un-bundling.

This is not a strategy-deck role. You will design experiments, partner with data scientists, navigate cross-functional complexity, and ship pricing changes that move the business. You'll work at the intersection of product, economics, and marketplace dynamics in one of the fastest-growing healthcare companies in the country.

You Will

• Own pricing experimentation end-to-end: Design, run, and analyze pricing experiments (payout levels, take rates, fee structures, incentive models) with proper controls and measurement.
• Price and package existing features: Identify opportunities to unbundle, tier, or price Headway's existing feature set as new revenue lines, while balancing the provider experience.
• Define Headway's pricing philosophy: Build a principled, defensible approach to how we set prices — transparent to providers, competitive in the market, and sustainable for the business.
• Inform tiering with pricing data: Partner with other product teams to ensure pricing and tier design are grounded in experimental evidence, willingness-to-pay research, and elasticity data.
• Build the experimentation infrastructure: Work with Engineering and Data to create systems that enable rapid, controlled pricing experiments across geographies and segments.
• Navigate cross-functional complexity: Align Finance, Provider Growth, Payer, Ops, and Legal around pricing decisions that affect every part of the business.

Who You Are

• 8+ years of PM experience, with at least 2-3 years owning pricing, monetization, or marketplace economics.
• You've personally owned pricing or packaging strategy and shipped changes that moved revenue.
• You've designed and run pricing experiments at scale — you know the difference between a feature A/B test and a pricing experiment.
• Strong quantitative fluency — you can partner with data scientists on experiment design and causal inference as a peer.
• You thrive in ambiguity and can build structure where none exists — this is a new team.
• Bonus: SaaS pricing & packaging experience (PLG, tiering, bundling).
• Bonus: You've worked in a two-sided marketplace or platform where pricing affects both supply and demand.
• Bonus: Healthcare or regulated industry experience.

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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.