Senior Principal, Sales Compensation Design & Strategy

Overview

Senior Principal, Sales Compensation Design & Strategy leads the design and management of Cloudflare's sales compensation plans across Sales, Technical Sales, Partner Sales, and Customer Success & Experience, serving as design authority on the Executive Compensation Steering Committee.

What you'll do

• Lead the sales compensation design process with the Executive Steering Committee, including CRO, CFO, and CPO level stakeholders.
• Drive C-level discussions on compensation philosophy, pay-for-performance outcomes, and strategic trade-offs; develop recommendation decks and own the narrative through approval.
• Architect new metrics aligned with Cloudflare's developer platform and AI product strategy (e.g., Workers consumption, AI Gateway adoption, platform attach, multi-product penetration).
• Create a 3-year roadmap for the Sales Compensation Design function.
• Build the AI Compensation Design Framework and Application to accelerate plan modeling, scenario simulation, payout forecasting, and what-if analysis.
• Leverage AI to design SPIFFs and incentive structures, including generating candidate designs, simulating seller behavior, and stress-testing against historical data before launch.
• Track ROI of comp plans, SPIFFs, and incentive programs using AI-driven analytics, moving from lagging reporting to predictive measurement.
• Develop AI-powered pay-for-performance reporting that surfaces real-time insights for executives, managers, and sellers.
• Collaborate with GTM Strategy, Operations, Finance, HR, IT, and Product to deploy compensation plans and GTM strategy.
• Lead compensation enablement and change management for the global Sales team, including AI-assisted communications, FAQ generation, and plan-acceptance workflows.
• Design SPIFFs and incentive strategies that balance long-term strategic bets with short-term revenue goals.
• Partner with Compensation Administration and Operations Teams to ensure design intent translates into accurate, auditable payouts.

What you'll need

• 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, through prior comp design work, analytics, or strategic projects.
• 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 presenting to and influencing C-level executives.
• Proven experience driving Executive Steering Committee meetings and owning the decision narrative end-to-end.
• Experience leading cross-functional initiatives to completion across Finance, HR, IT, Product, and GTM.
• Detail-oriented with a strategic mindset.
• Bachelor's degree required.

Nice to have

• Comfort building or directing the build of AI-powered internal applications.
• Strong background in sales strategy and compensation design with genuine curiosity about applying AI to transform the function.
• Exceptional stakeholder management skills, executive presence, and confidence to manage evolving strategies in a high-growth company.

Details

• Location: Remote, US.
• Applications accepted until October 13, 2026.
• Applicants who progress to the offer stage may be asked to attend an in-person interview at a Cloudflare Office or Hub.
• Role may require access to information protected under U.S. export control laws; offer may be conditioned on authorization to receive controlled software or technology without sponsorship for an export license.