Head of Pricing Strategy

About the 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.

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.
• 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.
• High bias for action, comfortable with ambiguity, and someone who takes full ownership of outcomes.

Pay & Benefits

Pay Transparency Disclosure: We use geographic cost of labor as an input to develop ranges for our roles and as such, each location where we hire may have a different range. If this role is remote, we have listed the top to the bottom of the possible range, but we will specify the target range for an exact location when you are selected for a recruiting discussion. For more information on our compensation philosophy, see our website.

On-target Earnings OR Base Salary range (San Francisco, CA): $202,000 - $261,800 USD

What We Offer

• A fast-paced and collaborative environment
• Learning and development allowance
• Competitive cash and equity compensation, and opportunity for advancement
• 100% medical, dental, and vision coverage
• Up to $25K reimbursement for fertility, adoption, and parental planning services
• Flexible PTO policy
• Monthly wellness stipend

At Checkr, we offer:

• An in-office work environment strengthens collaboration, drives innovation, and encourages connection.
• In-office perks are provided, such as lunch five times a week, a commuter stipend, and an abundance of snacks and beverages.
• A relocation stipend may be available for those willing to relocate to a Checkr hub location.

Equal Employment Opportunity

Checkr is committed to building the best product and company, which requires hiring talented and qualified individuals with a diverse set of perspectives and lived experiences. Checkr believes in hiring people of all backgrounds, including those whose histories are impacted by the justice system in accordance with local, state, and/or federal laws, including the San Francisco’s Fair Chance Ordinance.

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