Staff Product Manager, Monetization and Pricing

Hard Problems; United States; Remote; USD 180,000 - 260,000; Full time

Benefits offered by this job

Work-from-home stipend

Equity compensation

Professional development support

Job summary

Headway is seeking a dedicated pricing-focused Product Manager to own pricing as a systematic growth lever with a goal of generating $100M+ in revenue impact. You will design experiments, partner with data scientists, and ship pricing changes that touch providers, patients, and payers in a healthcare marketplace.

This is the first dedicated pricing PM role, requiring strong quantitative fluency, risk-aware experimentation, and collaboration with Finance, Legal, and Operations to scale pricing

Qualifications

• 8+ years in product management, with 2–3 years in pricing/monetization.
• Owned pricing or packaging strategy and shipped revenue-moving changes.
• Designed and ran pricing experiments at scale with data science input.
• Strong quantitative fluency and collaboration with data scientists.
• Experience in SaaS pricing and packaging (PLG, tiering, bundling).
• Healthcare or regulated-industry experience is a bonus.

Responsibilities

• Own pricing experimentation end to end: design, run, analyze.
• Identify opportunities to unbundle, tier, or price features as new revenue lines.
• Define pricing philosophy: transparent, competitive, sustainable.
• Partner with product, finance, and legal to ground decisions in evidence.
• Build experimentation infrastructure with engineering and data teams.
• Align with Finance, Provider Growth, Payer, Operations on pricing.

Skills

Pricing strategy

Monetization

Pricing experiments

Cross-functional collaboration

Data analysis

Two-sided marketplace

Healthcare knowledge

Job description

Headway is a Series D mental healthcare technology company with over $325M in funding from investors including a16z, Accel, and Spark Capital. Its mission is to make mental healthcare accessible to everyone by rebuilding the system around insurance acceptance. Headway has automated the administrative burden of running a therapy practice, including credentialing, claims, and payment reconciliation, and today more than 75,000 providers across all 50 states use its software to run their practices, collectively serving over one million patients. The company is moving beyond billing to become the platform where care actually happens, building tools for therapists, reimagining how patients find providers, and investing in the infrastructure to support this at scale.

The role

This is the first dedicated product management role focused on pricing at Headway. You would own pricing as a systematic, experimentation-driven growth lever with a stated goal of creating $100M or more in revenue impact. Pricing decisions at Headway touch every participant in the marketplace: what providers earn, what patients pay, and what payers reimburse. Today those decisions are made through a combination of analysis, intuition, and competitive benchmarking. Your mandate is to replace that with a rigorous, data-driven approach that generates evidence, builds conviction, and creates new revenue streams through bundling and unbundling. This is not a strategy-deck role. You would design and run experiments, partner closely with data scientists, navigate significant cross-functional complexity, and ship pricing changes that move the business. You would work at the intersection of product, economics, and marketplace dynamics.

What you would do

You would own pricing experimentation end to end, designing, running, and analyzing pricing experiments covering payout levels, take rates, fee structures, and incentive models, with proper controls and measurement frameworks. You would identify opportunities to unbundle, tier, or price Headway's existing feature set as new revenue lines while carefully balancing the provider experience. You would define Headway's pricing philosophy, building a principled and defensible approach to how prices are set that is transparent to providers, competitive in the market, and sustainable for the business. You would partner with other product teams to ensure that pricing and tier design are grounded in experimental evidence, willingness-to-pay research, and elasticity data. You would work with Engineering and Data to build the experimentation infrastructure needed to run rapid, controlled pricing experiments across geographies and segments. You would also align Finance, Provider Growth, Payer, Operations, and Legal around pricing decisions that affect every part of the business.

What they are looking for

Headway is looking for someone with eight or more years of product management experience, including at least two to three years owning pricing, monetization, or marketplace economics. You should have personally owned pricing or packaging strategy and shipped changes that moved revenue. You should have designed and run pricing experiments at scale and understand the meaningful differences between a feature A/B test and a pricing experiment. Strong quantitative fluency is required: you should be able to partner with data scientists on experiment design and causal inference as a peer. You should be comfortable building structure in ambiguous environments, as this is a new team with no established playbook. Experience with SaaS pricing and packaging, including product-led growth, tiering, and bundling, is a bonus. Experience working in a two-sided marketplace or platform where pricing affects both supply and demand is also a bonus, as is experience in healthcare or another regulated industry.

Working arrangements

The listing does not specify a location or remote or on-site arrangement, though a Work-from-Home Stipend is included in the benefits package, suggesting remote or hybrid working is supported.

Pay and benefits

Headway offers equity compensation as part of a comprehensive total rewards package.

• Additional benefits include medical, dental, and vision coverage, an HSA and FSA, a 401K, a work-from-home stipend, therapy reimbursement, 16 weeks of parental leave for eligible employees, Carrot Fertility annual reimbursement and membership, 13 paid holidays each year plus a Holiday Break between December 25th and December 31st, flexible paid time off, and an Employee Assistance Program.
• Training and professional development support is also provided.