Senior Principal, Sales Compensation Design & Strategy - Cloudflare

About the Role

The Global GTM Strategy, Planning and Operations team at Cloudflare supports our high-growth Sales organization through scalable, AI-supported GTM planning and operations. As the Senior Principal, Sales Compensation Design & Strategy, you will design and manage Cloudflare's Sales Compensation Plans across all customer-facing teams, including Sales, Technical Sales, Partner Sales, and Customer Success.

This is a high-visibility role with significant executive engagement, serving as the design authority on the Executive Compensation Steering Committee and leading discussions with the CRO, CFO, CPO, and COO.

Responsibilities

Executive Leadership & Design Authority

• Lead the Sales Compensation Design Process with the Executive Steering Committee.
• Drive C-level discussions on compensation philosophy, pay-for-performance outcomes, and strategic trade-offs.
• Architect new metrics that align seller incentives with Cloudflare's developer platform and AI product strategy (e.g., Workers consumption, AI Gateway adoption, platform attach).
• Create a 3-year roadmap for the Sales Compensation Design function.

AI-Native Compensation Design

• Build the AI Compensation Design Framework to accelerate plan modeling, scenario simulation, and payout forecasting.
• Leverage AI to design high-quality SPIFFs and incentive structures, simulating seller behavior and stress-testing against historical data.
• Track ROI of comp plans using AI-driven analytics to move from lagging reporting to predictive measurement.
• Develop AI-powered pay-for-performance reporting for real-time executive and manager insights.

Cross-Functional Execution

• Collaborate with GTM Strategy, Operations, Finance, HR, IT, and Product to ensure effective deployment of compensation plans.
• Lead compensation enablement and change management for the global Sales team.
• Partner with Compensation Administration and Operations to ensure design intent translates into accurate, auditable payouts.

Required Experience & Skills

• 15+ years of experience in Sales Compensation Design in a fast-paced tech company or as a management consultant.
• Demonstrated fluency with AI tools and AI-augmented workflows.
• Strong analytical skills, including the ability to architect new metrics for emerging business models (consumption, AI monetization).
• Exceptional presentation and communication skills, with proven experience influencing C-level executives.
• Experience leading cross-functional initiatives across Finance, HR, IT, Product, and GTM.
• Bachelor's degree required.

Benefits

• Comprehensive health, dental, and vision insurance.
• 401(k) retirement savings plan and Employee Stock Participation Plan.
• Flexible paid time off and robust leave programs.
• Fertility, family forming, and mental health support.