Senior Director Digital Native, Customer Engineering

Cloudflare•San Francisco, CA

About The Position

The Senior Director of Customer Engineering partners directly with the Area Vice President of Sales for Digital Native/AI to lead one of Cloudflare’s fastest-growing market segments. This business and technical leadership role is accountable for go-to-market motions and strategy, technical win rates, deal quality, customer outcomes across the full life cycle, and team effectiveness across the Digital Native portfolio. Working through managers and senior individual contributors, the leader sets the regional vision and execution standards, embeds AI-assisted execution and automated evaluation into sales engineering workflows, and engages strategically in critical customer moments to accelerate growth and impact. The role owns pre-sales technical strategy for high-velocity and enterprise-tier AI labs, developer platforms, and Digital Native scale-ups. It leads managers and technical teams, develops talent and operating models, partners with sales and cross-functional stakeholders, and represents the organization in customer, product, and partner engagements. The position is available in NYC, San Francisco, Los Angeles, or Chicago. Compensation varies by work location. The role is eligible for Cloudflare’s equity plan.

Requirements

At least 8 years of Customer Engineering leadership or enterprise sales leadership experience managing mid-to-large-sized technical organizations, including managing people managers in AI-assisted technical selling environments.
At least 8 years of hands-on experience as a Customer Engineer or Technical Consultant delivering complex SaaS, PaaS, or cloud security solutions.
A track record of partnering with Account Executives, Customer Success teams, and executive-level stakeholders to drive enterprise revenue and successful customer outcomes.
Demonstrable experience navigating, de-escalating, and resolving complex technical escalations, including use of automated escalation frameworks and cross-functional AI reviewer pipelines.
Strong experience supporting enterprise contract management, commercial negotiations, compliance, or project-management frameworks within the Digital Native segment.

Nice To Haves

Experience spanning financial consulting, software development, product management, or technical project delivery.
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 such as OpenCode or Windsurf.

Responsibilities

Partner with Digital Native Sales Leaders to develop and execute technical solution strategies, using AI-assisted architecture platforms and automated account-planning tools to create customized technical blueprints.
Lead, mentor, and coach frontline Customer Engineering Managers, setting standards for technical rigor, team culture, and hiring.
Define career-development pathways, succession planning, and performance-management frameworks for management and individual-contributor tracks.
Drive talent acquisition to recruit developer-native systems engineers and managers in a competitive AI talent market.
Own pre-sales technical strategy for high-velocity and enterprise-tier AI labs, developer platforms, and Digital Native scale-ups.
Partner with the AVP of Sales in Digital Native to drive pipeline conversion, strategy, technical win rates, incentive alignment, and quota attainment.
Set technical standards for edge and AI solution design, including Cloudflare Workers, Workers AI, Vectorize, Hyperdrive, R2, and edge inference pipelines.
Serve as executive sponsor on high-stakes Tier-1 deals, engaging directly with prospect CTOs, VP of Platform/Infrastructure leaders, and technical founders.
Design territory coverage, resource-allocation models, and account pod structures that balance high-touch strategic deals with scaled technical engagement.
Oversee and report on technical performance metrics, including win rates, deal quality, and team capacity, using automated evaluation pipelines over foundational data layers to improve execution.
Resolve regional issues in collaboration with global regional leads and use automated Customer Escalation AI Reviewers to streamline complex technical escalations.
Represent Digital Native Customer Engineering with executive stakeholders and collaborate with Product Management and Engineering to prioritize regional requirements and advocate for serverless and AI-driven security investments.
Partner with Channel, Global Systems Integrators, and local ecosystem partners to define joint technical strategies and scale market reach through automated solution frameworks.

Benefits

Medical/Rx insurance
Dental insurance
Vision insurance
Flexible Spending Accounts
Commuter Spending Accounts
Fertility and family-forming benefits
On-demand mental health support and Employee Assistance Program
Global travel medical insurance
Short- and long-term disability insurance
Life and 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
Equity plan participation