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 flexible work arrangements to support our team members' needs.