Chief of Staff to Chief Strategy Officer at cloudflare | AI Job Board

Job description

About Us

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 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 Magazine’s Top Company Cultures list and ranked among the World’s Most Innovative Companies by Fast Company.

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 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 you’re 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, you’ll fit right in.

Available Locations

San Francisco, CA
New York, NY

About the Team

The Strategy organization operates as a high-velocity engine at the intersection of business, technology, and go-to-market execution, driving enterprise growth, global expansion, market innovation, and strategic execution. Our multi-disciplinary team spans seven core strategic pillars: Network & Infrastructure Strategy, Industry Solutions, Strategic Partnerships, International Expansion, Executive Customer Engagements, Corporate Development & M&A, and the new business model of the Internet. As primary connective tissue across the enterprise, we collaborate closely with Sales, Product & Engineering, Finance, Legal, and Policy to translate corporate vision into measurable, real-world execution.

About the Role

We are seeking an exceptionally sharp, technically fluent Chief of Staff to serve as a key surrogate and strategic partner to our Chief Strategy Officer (CSO). In this role, you will act as a trusted extension of the CSO. You will regularly represent her authority in critical meetings, interface directly with technical leaders and key customers, craft high-impact strategic content, and drive operational alignment. You will ensure that departmental goals are prioritized, investments are optimized, and that teams are well aligned to deliver results. The ideal candidate is naturally curious, possesses deep technical product fluency, and brings the sharp business acumen required to step into the room on the CSO’s behalf at a moment's notice.

Responsibilities

Executive Representation: Act as a high-leverage surrogate for the CSO, attending key meetings and customer discussions on her behalf when she requires added executive coverage.
Strategic Advisory: Partner closely with the CSO as a strategic sounding board, leveraging data and sharp business instincts to simplify complex problems and keep executive focus on high-impact priorities.
Executive Communications & Writing: Translate high-level strategic vision, enterprise narratives, and complex technical data into executive and client-ready slide decks and comprehensive prep materials for high-stakes meetings. Draft strategic documents, internal communications, and executive social media posts on behalf of the CSO to drive thought leadership.
Enterprise Storytelling & Cadence: Help articulate the Strategy org’s impact internally across Cloudflare and externally in high-profile industry forums, while leading strategy retrospectives and All-Hands presentations.
Drive & Orchestrate Strategy-Led Initiatives: Help move complex, high-impact projects forward across the Strategy org. Monitor progress and timelines, follow up on critical action items across teams, and prepare executive updates to ensure alignment and execution.
Technical & Product Collaboration: Partner closely with Engineering, Product Management, Sales, and Marketing teams to understand our core product suite, navigate technical dependencies, and align cross-functional execution.

Desirable Skills, Knowledge, and Experience

Relevant Experience: 10+ years of combined experience across Investment Banking or Management Consulting and Big Tech, holding roles such as Technical Assistant, Product Manager, Business Development, Chief of Staff or similar.
Technical Aptitude & Product Fluency: Deep technical foundation with the ability to quickly grasp and translate complex technical concepts and products, effectively collaborating with engineering and technical product leaders.
Master-Level Communication & Writing Skills: Exceptional written and verbal skills; proven ability to write across multiple formats.
Executive Presence & Surrogate Authority: Proven track record of stepping into high-stakes meetings on behalf of executives, building instant credibility with C-suite stakeholders, enterprise customers, and board members.
Intellectual Curiosity & Analytical Mindset: Naturally curious problem solver who thrives on unraveling ambiguous technical and business challenges, distilling them into clear choices and actionable plans.
AI Fluency & Innovation: AI-native mindset with a genuine enthusiasm for leveraging AI tools, agentic workflows, and automation to streamline executive operations and drive team efficiency.
Willingness to Travel: Ability and willingness to travel 30–50% for customer meetings, industry conferences, and regional team syncs.

Compensation

Compensation may be adjusted depending on work location.

For Bay Area based hires: Estimated annual salary of $221,000- $304,000
For New York City based hires: Estimated annual salary of $211,000 - $290,000

Equity

This role is eligible to participate in Cloudflare’s equity plan.

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 Makes Cloudflare Special?

We’re not just a highly ambitious, large-scale technology company. We’re 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, we've equipped more than 2,400 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 Cloudflare’s 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, we've 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. Here’s the deal - we don’t 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 you’d like to be a part of? We’d 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 person's, 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.

Cloudflare provides reasonable accommodations to qualified individuals with disabilities. Please tell us if you require a reasonable accommodation to apply for a job. Examples of reasonable accommodations include, but are not limited to, changing the application process, providing documents in an alternate format, using a sign language interpreter, or using specialized equipment. If you require a reasonable accommodation to apply for a job, please contact us via e-mail at hr@cloudflare.com or via mail at 101 Townsend St. San Francisco, CA 94107.