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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. 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, and team effectiveness across the Digital Native portfolio. The leader will drive regional vision by embedding AI-assisted execution and automated evaluation layers into everyday sales engineering workflows, setting execution standards 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.
- 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.
Requirements
- 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.
- Prior experience spanning financial consulting, software development, product management, or technical project delivery.
- Strong existing relationships or familiarity with major Digital Native channel partners and global systems integrators.
- 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).
Skills
- AI-assisted architecture platforms
- Automated account planning tools
- Technical blueprints
- Technical rigor
- Team culture
- Talent acquisition
- Developer-native systems engineers
- AI talent market
- Pre-sales technical strategy
- High-velocity sales
- Enterprise-tier AI labs
- Developer platforms
- Digital native scale-ups
- Pipeline conversion
- Technical win rates
- Incentive alignment
- Quota attainment
- Edge solution design
- AI solution design
- Cloudflare Workers
- Workers AI
- Vectorize
- Hyperdrive
- R2
- Edge inference pipelines
- Executive sponsorship
- Tier-1 deals
- Territory coverage
- Resource allocation models
- Account pod structures
- Performance metrics
- Win rates
- Deal quality
- Team capacity
- Automated evaluation pipelines
- Foundational data layers
- International collaboration
- Cross-functional collaboration
- Regional issue resolution
- Global regional leads
- Automated Customer Escalation AI Reviewers
- Technical escalations
- Product roadmap influence
- Serverless capabilities
- AI-driven security capabilities
- Partner ecosystem cultivation
- Channel partners
- Global Systems Integrators (GSIs)
- Local ecosystem partners
- Joint technical strategies
- Automated solution frameworks
- Customer Engineering leadership
- Enterprise sales leadership
- Mid-to-large-sized technical organizations
- People management
- AI-assisted technical selling
- Hands-on Customer Engineering
- Technical Consulting
- Complex SaaS solutions
- PaaS solutions
- Cloud security solutions
- Strategic partnering
- Account Executives
- Customer Success teams
- Executive-level stakeholders
- Enterprise revenue generation
- Customer outcomes
- Escalation management
- Conflict resolution
- Automated escalation frameworks
- Cross-functional AI reviewer pipelines
- Enterprise contract management
- Commercial negotiations
- Compliance management
- Project management frameworks
- Financial consulting
- Software development
- Product management
- Technical project delivery
- Ecosystem knowledge
- Zero Trust architectures
- SASE architectures
- Application security frameworks
- Serverless developer platforms
- Modern AI development environments
- Automation environments
Location
- NYC
- SF
- LA
- Chicago
Work Type
- Onsite
- In-person interview may be required
Experience Level
- 8+ years of Customer Engineering leadership or enterprise sales leadership experience
- 8+ years of experience as a hands-on Customer Engineer or Technical Consultant
Salary/Compensations
- NYC: $312,000 - $491,000
- SF: $326,000 - $513,000
- California (Except SF): $312,000 - $491,000
- Chicago: $284,000 - $446,000
Benefits
- Equity participation in Cloudflare's equity plan
- 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
- Short and Long Term Disability Insurance
- Life & Accident Insurance
- 401(k) Retirement Savings Plan
- Employee Stock Participation Plan
- Flexible paid time off covering vacation and sick leave
- Leave programs, including parental, pregnancy health, medical, and bereavement leave
About the Company
- Cloudflare is on a mission to help build a better Internet.
- 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.
- Cloudflare values candidates who have the instinct to spot a 'normalized' problem and the AI-native curiosity to create a solution using the latest tools.
- The culture is built on iteration, leveraging AI to ship faster today to make it better tomorrow, while ensuring that every improvement is shared across the team.
- Cloudflare is not just a highly ambitious, large-scale technology company; it's a highly ambitious, large-scale technology company with a soul.
- Fundamental to its mission to help build a better Internet is protecting the free and open Internet.
- Project Galileo: Since 2014, Cloudflare has equipped more than 2,400 journalism and civil society organizations in 111 countries with powerful tools to defend themselves against attacks.
- Athenian Project: In 2017, Cloudflare 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.
- 1.1.1.1: Cloudflare 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.
- Cloudflare does not store client IP addresses and will not sell user data to advertisers or use it to target consumers.
Equal Opportunity
- 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.
- 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.