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 worlds 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 Internet application online without adding hardware installing software or changing a line of code. Internet properties powered by Cloudflare all have web traffic routed through its intelligent global network which gets smarter with every request. As a result they see significant improvement in performance and a decrease in spam and other attacks. Cloudflare was named to Entrepreneur Magazines Top Company Cultures list and ranked among the Worlds Most Innovative Companies by Fast Company.

At Cloudflare were not looking for people who wait for a polished roadmap; were 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 using the latest tools. Our culture is built on iteration leveraging AI to ship faster today to make it better tomorrow while ensuring that every improvement no matter how small is shared across the team to lift everyone up. If youre the type of person who values curiosity over bureaucracy and that AI is a partner in solving tough problems to keep the Internet moving forward youll fit right in.

• US

Applications will be accepted until October 13 2026.

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. We focus on thoughtful planning of sales capacity segmentation territory carving quota setting and compensation design while ensuring clear rules of engagement for our Sales Team. Our goal is to establish a cohesive consistent process framework that can support high growth enable the Companys strategy and accelerate Cloudflares leadership in the developer and AI-native business segments.

As the Senior Principal Sales Compensation Design & Strategy you will design and manage Cloudflares 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 Cloudflares 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.

Responsibilities

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 Cloudflares 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.

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 - 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.
• Bachelors degree required.

Bonus Points

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.

Compensation may be adjusted depending on work location.

• For San Francisco based hires: Estimated annual salary of $230000 - $317000
• For California (excluding Bay Area) Washington Washington DC NY and NJ based hires: $220000 - $303000
• For Colorado based hires: Estimated annual salary of $200000 - $275000

This role is eligible to participate in Cloudflares equity plan.

Cloudflare offers a complete package of benefits and programs to support you and your family. Our benefits programs can help you pay health care expenses support caregiving build capital for the future and make life a little easier and fun! The below is a description of our benefits for employees in the United States and benefits may vary for employees based outside the U.S.

Health & Welfare Benefits

• Medical/Rx Insurance
• Dental Insurance
• Vision Insurance
• Flexible Spending Accounts
• Commuter Spending Accounts
• Fertility & Family Forming Benefits
• On-demand mental health support and Employee Assistance Program
• Global Travel Medical Insurance

Financial Benefits

• Short and Long Term Disability Insurance
• Life & Accident Insurance
• 401(k) Retirement Savings Plan
• Employee Stock Participation Plan

Time Off

• Flexible paid time off covering vacation and sick leave
• Leave programs including parental pregnancy health medical and bereavement leave

Were not just a highly ambitious large-scale technology company. Were a highly ambitious large-scale technology company with a soul. Fundamental to our mission to help build a better Internet is protecting the free and open Internet.

Project Galileo: Since 2014 weve equipped more than 2400 journalism and civil society organizations in 111 countries with powerful tools to defend themselves against attacks that would otherwise censor their work technology already used by Cloudflares enterprise customers--at no cost.

Athenian Project: In 2017 we created the Athenian Project to ensure that state and local governments have the highest level of protection and reliability for free so that their constituents have access to election information and voter registration. Since the project weve provided services to more than 425 local government election websites in 33 states.

1.1.1.1: We released 1.1.1.1 to help fix the foundation of the Internet by building a faster more secure and privacy-centric public DNS resolver. This is available publicly for everyone to use - it is the first consumer-focused service Cloudflare has ever released. Heres the deal - we dont store client IP addresses never ever. We will continue to abide by our privacy commitment and ensure that no user data is sold to advertisers or used to target consumers.

Sound like something youd like to be a part of Wed love to hear from you!

Please note that applicants who progress to the offer stage of the interview process may be asked to attend an in-person interview within one of the Cloudflare Offices or Cloudflare Hubs. More details about this will be available at that stage of the interview process.

This position may require access to information protected under U.S. export control laws including the U.S. Export Administration Regulations. Please note that any offer of employment may be conditioned on your authorization to receive software or technology controlled under these U.S. export laws without sponsorship for an export license.

Cloudflare is proud to be an equal opportunity employer. We are committed to providing equal employment opportunity for all people and place great value in both diversity and inclusiveness. All qualified applicants will be considered for employment without regard to their or any other persons perceived or actual race color religion sex gender gender identity gender expression sexual orientation national origin ancestry citizenship age physical or mental disability medical condition family care status or any other basis protected by law. We are an AA/Veterans/Disabled Employer.

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