Head of Pricing

About this role

Drata is building the trust layer between great companies - automating compliance, managing risk, and helping organizations prove trust continuously as they scale. We're Dratanauts: a global crew of 600+ professionals united by a culture that rewards integrity, ownership, and raising the bar, no matter where in the world we're working from.

Why Join the Drata Team? At Drata, you're not maintaining legacy compliance software - you're building the agentic AI platform defining what trust looks like for the next generation of companies. Here's what makes the work itself worth showing up for:

- Problems without a playbook: You'll work at the edge of AI and security, building agentic governance, continuous compliance, and real-time trust verification to solve problems that don't have an established answer yet. You're writing it as you go.

- Real ownership, not just process: Our values center on owning outcomes and raising the bar, not checking boxes. You're expected to have opinions and back them.

- A seat at the table: Your perspective is unique and valued. Open debate and diverse viewpoints are built into how decisions actually get made here, at every level.

- Growth at rocketship speed: Drata is scaling fast, which means scope grows fast too. High performers get more ownership, visibility, and experience.

- A crew, not just coworkers: Dratanauts consistently describe a "come as you are" culture with sharp, curious people—the kind of team that makes hard problems genuinely fun to solve. See what they say here https://drata.com/about/careers/life and follow us on LinkedIn https://www.linkedin.com/company/drata/posts/?feedView=all for company news, employee stories, and career updates.

Job Summary:

We are looking for a Head of Pricing to own pricing and packaging at one of the most consequential moments in Drata's history. The software industry is in the middle of a generational shift, from products built around human users to products built around AI agents that do work end-to-end. The commercial models that powered SaaS for the last fifteen years were built for a world where value scaled with seats. That world is ending. The companies that figure out how to price AI-native software will define the next decade of the category, and the ones that do not will leave compounding value on the table at every renewal and every enterprise deal.

This is the role that owns Drata's answer. You will design and roll out the pricing model for an agent-first platform, lead the transition of an existing subscription book toward dynamic monetization, and build the commercial and technical foundation that the entire company plans against. This role reports to the Chief Product & Technology Officer and works directly with the CEO, CFO, and CRO.

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 plat

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