Head of Pricing

Drata•San Francisco, CA

4d•$207,700 - $281,000•Hybrid

About The Position

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.

Requirements

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. You do not need to write the code, but you need to understand the stack well enough to design pricing models that are operable in it and to be a credible partner to Engineering.
Demonstrated experience partnering with a Billing function on the operational side: invoicing, dunning, true-ups, dispute handling, and the day-to-day mechanics of running a consumption-based book.
Track record of building pricing frameworks and decision tools that product teams use directly to launch new SKUs, rather than every pricing decision routing through a central team.
Demonstrated ability to operate across Product, Finance, Sales, Customer Success, Engineering, and Billing, and to bring those functions into alignment on contentious commercial decisions.
Excellent written communication, with experience writing strategy documents and pricing narratives that executive teams and boards can act on.
A clear point of view on how AI is changing software monetization, informed by direct exposure to companies on the frontier of this shift.
Experience leading large enterprise deal structures and a comfort engaging directly with customer economic buyers when it matters.
Bachelor's degree required; MBA or equivalent analytical background a plus.

Nice To Haves

Pricing leadership at an AI-native software company that ships agent-based or copilot-based products, where you owned the commercial model from first principles rather than inheriting a SaaS playbook.
Experience pricing software that meters value at the work-unit level (per job, per resolution, per outcome, per token-with-margin) and reconciling that with enterprise procurement expectations.
Direct experience working with modern billing platforms (e.g., Metronome, Orb, Stripe Billing, Zuora, m3ter) or building a comparable internal system.
Time spent at a public software company that completed a successful pricing model transition, where you saw the gross margin, ARR, and Wall Street narrative implications play out at scale.
Prior experience as a product manager, financial analyst, or strategy consultant before moving into pricing, with the rigor that background brings to commercial modeling.
Active engagement with the pricing community writing publicly about AI monetization (posts, talks, frameworks), and a track record of forming a view before consensus settles.

Responsibilities

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.
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.
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.
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.
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.
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.

Benefits

Stock equity
Up to 100% employer-paid premiums for medical, dental, and vision coverage for employees and their dependents
Comprehensive wellness benefits and healthcare concierge services
401(k) plan
Company-paid life and disability insurance
Tax-advantaged spending accounts
Discounted voluntary offerings
Paid Parental Leave policy, after six months of employment
Kindbody fertility and family-building benefits
Dedicated leave specialists
Generous annual stipends for both professional and personal development
Access to a wide range of internal learning opportunities
Flexible vacation policy
Paid holidays