Staff Product Manager, Monetization and Pricing

About the role

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.

Additional information

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.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

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