Senior Director Digital Native, Customer Engineering

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).