Senior Director Digital Native, Customer Engineering

Cloudflare•Austin, TX

4d•$284,000 - $513,000

About The Position

The Senior 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 member of the leadership team, this business and technical leader is accountable for go-to-market motions and strategy, technical win rates, deal quality, customer outcomes across the full lifecycle, and team effectiveness across the Digital Native portfolio. The role operates through managers and senior individual contributors, establishing execution standards and engaging strategically in critical customer moments to accelerate growth and impact. It also embeds AI-assisted execution and automated evaluation layers into everyday sales engineering workflows. The role owns pre-sales technical strategy for high-velocity and enterprise-tier AI labs, developer platforms, and Digital Native scale-ups. It sets technical standards for edge and AI solution design, sponsors high-stakes deals, shapes territory coverage and resource models, and oversees technical performance. The leader works across Sales, Product, Engineering, Customer Success, Channel, GSIs, partners, and international regional teams to improve customer outcomes, resolve escalations, influence product priorities, and expand Cloudflare’s reach. The position is available in New York City, San Francisco, Los Angeles, or Chicago. Compensation varies by location: $312,000–$491,000 in New York City; $326,000–$513,000 in the San Francisco Bay Area; $312,000–$491,000 elsewhere in California; and $284,000–$446,000 in Chicago. The role is eligible for Cloudflare’s equity plan. U.S. benefits include health and welfare, financial, and time-off programs. Applicants who reach the offer stage may be asked to attend an in-person interview at a Cloudflare office or hub. The position may require access to information controlled under U.S. export laws, and an offer may be conditioned on export authorization without sponsorship for a license.

Requirements

At least 8 years of Customer Engineering leadership or enterprise sales leadership experience managing mid-to-large-sized technical organizations, including experience 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.
Proven ability to partner with Account Executives, Customer Success teams, and executive stakeholders to drive enterprise revenue and successful customer outcomes.
Demonstrated experience navigating, de-escalating, and resolving complex technical escalations.
Strong experience supporting enterprise contract management, commercial negotiations, compliance, or project management frameworks within the Digital Native segment.
Experience managing first-line engineering or pre-sales managers and scaling teams through rapid headcount growth.

Nice To Haves

Background 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 design technical blueprints for clients.
Lead, mentor, and coach frontline Customer Engineering managers, establishing standards for technical rigor, team culture, and hiring.
Define career development pathways, succession planning, and performance management frameworks for management and individual-contributor tracks.
Develop talent acquisition strategies to recruit developer-native systems engineers and managers.
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 and engage with prospect CTOs, platform or infrastructure leaders, and technical founders.
Design territory coverage, resource allocation models, and account pod structures that balance strategic deals with scaled technical engagement.
Oversee and report on Digital Native technical performance metrics, including win rates, deal quality, and team capacity, using automated evaluation pipelines to improve execution.
Collaborate with global regional leads to identify and resolve regional issues, using automated Customer Escalation AI Reviewers to streamline complex technical escalations.
Represent Customer Engineering at the executive level and work 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.
Navigate, de-escalate, and resolve complex technical escalations in collaboration with cross-functional teams.

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