Senior Director Digital Native, Customer Engineering

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 pr