Head of Pricing

What you'll do

Pricing strategy and model design

• Own Drata's end-to-end pricing and packaging strategy across the product portfolio, including the design and rollout of consumption, outcome-based, hybrid, and platform-tier monetization models for AI-native products.
• Build the analytical foundation that connects unit economics, agent run cost, willingness-to-pay, gross margin, and customer value into a single coherent commercial model.
• Develop and own Drata's point of view on how AI-native software should be priced, translate that into specific, defensible constructs the company takes to market, and revise it as the category evolves.
• Lead competitive pricing intelligence across GRC, security, and AI software more broadly, including frontier monetization experiments at AI-native companies, and pressure-test Drata's positioning against it.

Pricing frameworks and product team enablement

• Build the pricing frameworks, decision rubrics, and model templates that product teams use to monetize new capabilities, so that pricing scales with the product portfolio rather than bottlenecking on a single team.
• Establish the standards and guardrails for how product teams design and launch new SKUs, including the discovery process, validation methodology, packaging conventions, and approval workflow.
• Partner with product leaders to coach them through pricing decisions for their own surfaces, raising the pricing fluency of the broader product organization over time.
• Maintain the catalog of active SKUs, entitlements, and meters, and own the lifecycle of how new ones are introduced, retired, or repriced.

Transition from subscription to dynamic monetization

• Lead the multi-quarter plan to evolve Drata's existing subscription book toward the new model, protecting current revenue while accelerating the new motion.
• Design migration paths, grandfathering rules, and renewal mechanics that maintain customer trust while moving the book.
• Partner with Finance to model gross margin, ARR, and forecasting implications across the transition, and own the commercial inputs to long-range planning.

Billing systems and technical foundation

• Partner closely with the Billing, Revenue Operations, and Engineering teams to ensure pricing models are accurately metered, billed, invoiced, and recognized end-to-end.
• Bring a working technical understanding of how usage-based billing systems operate, including event metering, rating engines, entitlement enforcement, proration, overage handling, and revenue recognition under consumption models.
• Co-own the requirements and design partnership with Engineering on the internal billing and metering platform, ensuring it can support the pricing models the business needs to launch.
• Make sure every commercial construct introduced is operable in the billing stack before it ships to customers.

Packaging across segments

• Design packaging that flexes across customer segments, from emerging growth to large enterprise, with a single coherent model.
• Define product bundling, tiering, and entitlement logic in partnership with Product and Engineering, ensuring pricing is metered and enforceable in the platform itself.
• Own list pricing, discounting frameworks, and approval thresholds in partnership with Revenue Operations and Deal Desk.

Cross-functional leadership

• Partner with Sales and Customer Success on strategic deal structure, especially for large enterprise opportunities where standard pricing constructs are being tested at the edges.
• Equip GTM teams with the narrative, tools, and training to sell new commercial models with confidence.
• Build and lead the function over time, starting hands-on and scaling the team as the model matures.

What you'll bring

• 10+ years of experience in pricing, monetization, or commercial strategy at B2B software companies, with at least one full cycle of leading a major pricing model transition (subscription to consumption, seat-based to usage-based, or platform repricing).
• Direct, hands-on experience designing and rolling out consumption-based, outcome-based, or AI-native pricing models at companies past $100M ARR.
• Strong analytical foundation, with the ability to build the financial model yourself and reason fluently about unit economics, cost-to-serve, gross margin, willingness-to-pay, and elasticity.
• Working technical understanding of usage-based billing infrastructure, including event metering, rating, entitlements, proration, overage, and revenue recognition.
• Demonstrated experience partnering with a Billing function on the operational side: invoicing.