Senior Director Digital Native, Customer Engineering

Location: Hybrid 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: NYC, SF, LA, Chicago About the Role The Sr. Director of Customer Engineering will partner directly with the Area Vice President of Sales for Digital Native/AI to lead one of Cloudflare’s fastest-growing market segments. As a key member of the leadership team, this role serves as a business and technical leader accountable for go to market (GTM) motions and strategy, technical win rates, deal quality, customer outcomes / full life cycle, and team effectiveness across the entire Digital Native portfolio. Operating through managers and senior individual contributors, this leader will drive the regional vision by embedding AI-assisted execution and automated evaluation layers into everyday sales engineering workflows, setting the standards for execution while strategically engaging in critical customer moments to accelerate growth and impact. Responsibilities Drive Regional Strategy: Partner with Digital Native Sales Leaders to develop and execute technical solution strategies, leveraging AI-assisted architecture platforms and automated account planning tools to design customized technical blueprints for Digital Native clients. Lead, mentor, and coach frontline CE Managers, instilling high standards for technical rigor, team culture, and hiring. Proven experience managing first-line engineering or pre-sales managers, with a track record of scaling teams through rapid headcount growth. Define career development pathways, succession planning, and performance management frameworks across both the management and IC tracks. Drive talent acquisition strategy to recruit top-tier, developer-native systems engineers and managers in a competitive AI talent market Own the pre-sales technical strategy for high-velocity and enterprise-tier AI labs, developer platforms, and digital native scale-ups. Partner closely with the AVP of Sales in Digital Native to drive pipeline conversion, strategy, technical win rates, incentive alignment and quota attainment. Set the technical standard for edge and AI solution design (Cloudflare Workers, Workers AI, Vectorize, Hyperdrive, R2, and edge inference pipelines). Serve as executive sponsor on high-stakes, Tier-1 deals, meeting directly with prospect CTOs, VP of Platform/Infra, and technical founders. Design optimal territory coverage, resource allocation models, and account pod structures balancing high-touch strategic deals with scaled technical touchpoints. Own Performance Metrics: Oversee and report on Digital Native technical performance metrics—including win rates, deal quality, and team capacity—utilizing automated evaluation pipelines over foundational data layers to continuously elevate execution bars. Collaborate Internationally and Cross-Functionally: Swiftly identify and resolve regional issues by collaborating with global regional leads and deploying automated Customer Escalation AI Reviewers to streamline complex technical escalations. Influence the Product Roadmap: Represent the Digital Native Customer Engineering organization at the executive level, collaborating with Product Management and Engineering teams to prioritize regional requirements and advocate for investments in serverless and AI-driven security capabilities. Cultivate Partner Ecosystems: Partner closely with Channel, Global Systems Integrators (GSIs), and local ecosystem partners across the Digital Native segment to define joint technical strategies and scale Cloudflare’s market reach through automated solution frameworks. Desirable Skills, Knowledge, and Experience Must-Have Skills Proven Leadership Experience: 8+ years of Customer Engineering leadership or enterprise sales leadership experience managing mid-to-large-sized technical organizations, including experience managing people managers within AI-assisted technical selling environments. Technical Background: 8+ years of experience as a hands-on Customer Engineer or Technical Consultant delivering complex SaaS, PaaS, or cloud security solutions. Strategic Partnering: A proven track record of successfully partnering with Account Executives, Customer Success teams, and executive-level stakeholders to drive enterprise revenue and successful customer outcomes. Escalation & Conflict Resolution: Demonstrable experience in successfully navigating, de-escalating, and solving complex technical escalations, utilizing automated escalation frameworks and cross-functional AI reviewer pipelines. Enterprise Contract & Process Management: Strong experience supporting enterprise contract management, commercial negotiations, compliance, or project management frameworks within the Digital Native Segment. Bonus Points Diverse Industry Background: Prior experience spanning financial consulting, software development, product management, or technical project delivery. Ecosystem Knowledge: Strong existing relationships or familiarity with major Digital Native channel partners and global systems integrators. Advanced Technical Credibility: Hands-on familiarity with Zero Trust/SASE architectures, application security frameworks, serverless developer platforms, or modern AI development and automation environments (e.g., OpenCode, Windsurf). Compensation Compensation may be adjusted depending on work location. For New York City based hires: Estimated annual salary of $312, 000 - $491,000. For San Francisco Bay Area based hires: Estimated annual salary of $326,000 - $513,000. For California based hires (Except San Francisco): Estimated annual salary of $312,000 - $491,000. For Chicago based hires: Estimated annual salary of $284,000 - $446,000. 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 ea sier 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 Fe rtility & 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 P lan Employee Stock P articipation Plan Time Off Flexible paid time off covering vacation and sick leave Leave programs, i ncluding 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.