Senior Principal, Sales Compensation Design & Strategy

At Cloudflare, we are on a mission to help build a better Internet. Today the company runs one of the world’s largest networks that powers millions of websites and other Internet properties for customers ranging from individual bloggers to SMBs to Fortune 500 companies. Cloudflare protects and accelerates any Intern...

At Cloudflare, we’re not looking for people who wait for a polished roadmap; we’re looking for the builders who see the cracks in the Internet that everyone else has simply learned to live with. We value candidates who have the instinct to spot a "normalized" problem and the AI-native curiosity to create a solution ...

The Global GTM Strategy, Planning and Operations team at Cloudflare supports our high-growth Sales organization through scalable, AI supported GTM planning and operations. We focus on thoughtful planning of sales capacity, segmentation, territory carving, quota setting, and compensation design while ensuring clear r...

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 & Experience, to ensure they are motivating, aligned with Cloudflare's strategy, and industry leading. This is a high visibility role with significant executive engagement, including leading C-level discussions with our CRO, CFO, CPO, and COO, and serving as the design authority on the Executive Compensation Steering Committee.
You will architect new compensation metrics that reflect how Cloudflare monetizes a developer first, AI supportive business - including consumption, adoption, and platform attach - and ensure roles, territories, and quotas align with compensation plans to achieve our GTM objectives. You will establish a governance framework for efficient compensation planning and partner closely with the Compensation Administration and Operations Teams to ensure effective implementation and accurate payouts. A strong understanding of SaaS bookings, monetization approaches, and consumption and adoption models is essential.
The scope of executive influence, the architectural work required to support our developer/AI business model, and the AI-native transformation of the compensation design function make this seat fundamental to our GTM execution strategy. 
Executive Leadership & Design Authority
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 that align seller incentives 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.

AI-Native Compensation Design
Build the AI Compensation Design Framework and Application - an internal capability that uses AI to accelerate plan modeling, scenario simulation, payout forecasting, and what-if analysis across thousands of sellers and territories.
Leverage AI to design high-quality 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 of plan effectiveness, seller behavior change, and revenue lift.
Develop AI-powered pay-for-performance reporting that surfaces insights for executives, managers, and sellers in real time, replacing static quarterly reviews with continuous intelligence.

Cross-Functional Execution
Collaborate with GTM Strategy, Operations, Finance, HR, IT, and Product to ensure effective deployment of 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 the Compensation Administration and Operations Teams to ensure design intent translates into accurate, auditable payouts.

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 - whether through prior comp design work, analytics, or strategic projects. Comfort building or directing the build of AI-powered internal applications is strongly preferred.
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.

The ideal candidate combines a strong background in sales strategy and compensation design with genuine curiosity about applying AI to transform the function. Candidates will have exceptional stakeholder management skills, executive presence, and the confidence to manage evolving strategies in a high-growth company.