Vice President, Strategy and Planning

Cloudflare • San Francisco, CA

6d

About The Position

Cloudflare is seeking an executive-level leader to head the Strategy & Planning organization, responsible for architecting and orchestrating the long-term strategic direction of the global Revenue organization. This leader will report to our Worldwide VP of Revenue Operations and will serve as a senior advisor to the CRO and executive leadership team, shaping multi-year growth strategy, driving operational excellence, and ensuring that our go-to-market (GTM) engine is optimized for scale, efficiency, and sustained revenue performance. This role owns Cloudflare’s end-to-end revenue planning architecture — including corporate GTM strategy, multi-year financial planning, annual planning, data governance, compensation design, and alignment across Sales, Marketing, Product, Finance, and Operations. The VP will guide strategic decision-making at the highest levels, translate corporate priorities into executable plans, and build world-class processes that support Cloudflare’s next phase of growth. You are right for this role if you are a strategic operator with a deep understanding of GTM dynamics in high-growth technology companies, a strong executive presence, exceptional cross-functional leadership skills, and the ability to balance long-term vision with pragmatic execution. You thrive in ambiguity, drive alignment across senior stakeholders, and lead with clarity, data, and influence.

Requirements

• 15+ years of experience in GTM strategy, revenue operations, corporate strategy, or related operational leadership roles within high-growth technology companies
• Demonstrated success influencing C-level executives and driving alignment across complex global organizations
• Track record of owning and delivering multi-year strategic plans and enterprise-level transformations
• Exceptional operational rigor with proven experience leading large, cross-functional programs in fast-moving environments
• Outstanding executive communication skills, with the ability to simplify complexity, tell a strategic story, and drive decisions
• Deep quantitative fluency and ability to synthesize data into actionable strategic insights
• Experience leading multi-disciplinary teams, including contractors, offshore resources, and specialized strategy, analytics, or planning roles
• Comfortable operating in high ambiguity; able to drive clarity, structure, and disciplined execution
• Strong influencing, conflict-resolution, and negotiation skills at the executive level

Responsibilities

• Enterprise GTM Strategy Leadership Provide the strategic vision and executive leadership for Cloudflare’s global go-to-market strategy across products, customer segments, geographies, and routes to market. Ensure GTM strategy tightly aligns with corporate goals, market opportunities, and long-term revenue ambitions.
• Multi-Year Strategic & Financial Planning Own the creation and continuous refinement of Cloudflare’s long-range revenue plan, including revenue architecture, investment frameworks, operating models, and resource strategy. Partner with Finance to ensure an integrated, data-driven plan that supports scalability and profitability.
• Annual GTM Planning & Operating Cadence Lead Cloudflare’s end-to-end annual planning process, including revenue targets, quota deployment, coverage models, segmentation, headcount allocation, and market investment priorities. Establish the planning rhythm of the business and hold senior leaders accountable to milestones and outcomes.
• Rules of Engagement & Organizational Alignment Set and govern the policies, frameworks, and cross-functional engagement models that define how Sales, Marketing, Customer Success, Partnerships, and other functions collaborate. Ensure clarity, reduced friction, and alignment across the entire revenue ecosystem.
• Sales Effectiveness, Performance, & Productivity Responsible for designing and executing strategies that align sales processes, technology, and data to drive productivity improvements and efficiency within the GTM organization at Cloudflare. Run a team that defines the executive dashboards, analytics frameworks, and KPIs that measure the health and performance of the GTM engine. Uses data driven insights to advise CRO and executive leadership on performance trends, productivity opportunities, and strategic interventions.
• Compensation Strategy & Design Oversee the design of global compensation frameworks that reinforce strategic priorities, drive rep productivity, reward the right behaviors, and ensure fairness, transparency, and alignment with corporate financial objectives. Partner closely with Finance, HR, and Sales Leadership.
• Data Strategy & Governance for GTM Systems Define the enterprise data governance model for GTM systems, ensuring data quality, consistent definitions, and trustworthy insights across the revenue organization. Collaborate with IT, BI, and Product to build scalable data and systems infrastructure.
• Executive-Level Cross-Functional Partnership Work closely with the CRO, CFO, CMO, CPO, Business Intelligence, and Product leadership teams to ensure Cloudflare’s GTM strategy, operational plan, and product roadmap are integrated and mutually reinforcing. Influence executive decision-making with clear, data-driven insights.
• Build & Lead a High-Performing Organization Attract, develop, and lead a world-class Strategy & Planning organization. Set the vision, elevate capabilities, and drive a culture of accountability, transparency, innovation, and operational excellence.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed
• Number of Employees: 1,001-5,000 employees