Staff Product Manager, Pricing

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.

Responsibilities

• 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.

Requirements

• 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.

Qualifications

• 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.

Skills

• Strong quantitative fluency
• Ability to partner with data scientists
• Experience designing and running pricing experiments at scale
• Ability to navigate cross-functional complexity

Benefits

• 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

Pay

We offer a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity.

Schedule

We are committed to offering a flexible schedule to accommodate the diverse needs of our team members.