Aimed at mid-level pricing strategists who thrive in high-velocity environments and can design AI-native commercial models, with hybrid work in San Francisco.
Derived from job-description analysis by Serendipath's career intelligence engine.
Original posting from Drata via Ashby
Our Mission & Values:
At Drata, we help companies earn and keep the trust of their users, customers, partners, and prospects. We’re the proof layer that shows great companies deserve the trust they aim to build.
We live our values every day. Built on Trust means consistency is everything. Act with Integrity by always doing the right thing. Being Customer-Obsessed keeps the people we serve at the center of our work. Competitive Fire drives us to push ourselves harder than anyone else. Diversity brings unique perspectives that lead to better solutions. Automation First ensures we save time and money by making efficiency a priority.
Our Culture & Work Style 🚀
At Drata, we’re not just building software - we’re building a mindset. Everything we do springs from:
- Be a Driver (Owner‑Operator Mentality): Own your work. Improve relentlessly. Deliver results.
- Move at Drata Speed (Precision & Velocity): Fast decisions. Quick learning. Immediate impact.
- Stay Mission-Driven (Customer‑Obsessed): Challenge assumptions. Deliver value. Stay hungry.
We pair that high-velocity culture with a thoughtful hybrid model because we believe flexibility and collaboration both matter. That’s why in the Bay we come together in-office Tuesday through Thursday our high‑impact collaboration days where teams align, strategize, and innovate. Mondays and Fridays are flexible, giving you space for focused work, balance, and autonomy.
If you thrive when you’re empowered, energized, and working with smart, mission-driven people, you’ll feel at home here.
Why Join The Drata Team?
The best way to understand the Driver’s Mindset is to see it in action. We’re an award-winning, mission-driven team of 600+ people worldwide, united by a culture that values trust, speed, and continuous growth.
- See the Speed: https://www.youtube.com/watch?v=QidTdkGwKMY Watch our CEO, Adam Markowitz, discuss the hyper-growth journey, from $0 to $100M ARR in just four years
- Hear the Voice of the Team https://drata.com/about/life-at-drata: Explore our "Life at Drata" page for employee testimonials on our collaborative and the growth opportunities available.
- Experience the Impact https://www.greatplacetowork.com/certified-company/7044563: See why we are consistently recognized on Fortune's Best Workplaces lists.
- Connect with Us on Socials: LinkedIn https://www.linkedin.com/company/drata/posts/?feedView=all - follow us for company updates, employee stories, and career news.
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 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 bi
Source: Drata careers (Ashby)