Head of Pricing Strategy

About the team/role

We are looking for a Head of Pricing Strategy to build our pricing strategy function. Pricing is one of the highest-leverage decisions a company makes, and at Checkr it’s genuinely complex. We have multiple go-to-market motions, a growing portfolio of acquired businesses, thousands of SKUs with complex configuration and packaging permutations, and we’re building new products that serve new use cases. We’re looking for someone to build this function, drive the decisions, and make a measurable impact on how Checkr captures value across its entire product portfolio.

What you’ll do

• Own pricing and packaging strategy across all products and go-to-market channels, from high-touch enterprise to self-serve, and drive successful execution across the organization.
• Build pricing models for new and existing products across customer segments, including consumption-based and outcome-based structures that account for customer value and our product economics.
• Run rigorous pricing research, including conjoint analysis, Van Westendorp price sensitivity studies, economic value driver analysis, and willingness-to-pay interviews, to support pricing decisions and build organizational confidence in them.
• Design and run pricing experiments; track and analyze price elasticity, cross-price elasticity, packaging performance, and customer purchasing behavior to inform broader rollouts.
• Build a pricing strategy function that uses AI-powered research, automated analysis, and modern tooling to operate at a speed and scale that accelerates innovation.
• Build pricing and packaging architecture that remains coherent and durable as we launch new products, acquire companies, and scale across channels.
• Partner with Product, Sales, Marketing, Deal Desk, and Go-to-Market leadership to price new offerings and evolve existing ones. Own pricing governance and keep decisions moving at the speed of the business.
• Track competitive pricing dynamics and market trends on an ongoing basis, and surface actionable insights as things evolve.
• Define pricing KPIs, build the infrastructure to track them, and communicate performance and recommendations clearly to senior leadership.

What you bring

• 8+ years of experience, with 5+ years in B2B pricing and packaging across product-led growth and enterprise sales motions. Experience with consumption business models or businesses with real COGS is a plus.
• Hands-on experience with pricing research methodologies: conjoint analysis, Van Westendorp, discrete choice experiments, and customer willingness-to-pay interviews. You know which tool fits which problem.
• A track record of building and launching pricing models that drove measurable results across multiple customer segments.
• Strong financial modeling skills and comfort working with large datasets. SQL experience is a plus.
• Proven ability to work across Product, Sales, Finance, and Executives to build alignment and move decisions forward.
• Can take complex analytical work and turn it into a clear, executive-ready recommendation.
• High bias for action, comfortable with ambiguity, and someone who takes full ownership of outcomes.