Director, Customer Engineering

About this role

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: Canada

About the Role

The Director of Customer Engineering will partner directly with the Vice President of Sales for Canada to lead one of Cloudflare’s fastest-growing enterprise market segments. As a key member of the Canadian leadership team, this role serves as a business and technical leader accountable for technical win rates, deal quality, customer outcomes, and team effectiveness across the entire Canadian 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 Canadian 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 Canadian clients.

• Lead and Scale the Team: Recruit, interview, and onboard new team members while managing overall capacity, equitable workload distribution, and optimizing team productivity through AI-driven operational tools.

• Foster Professional Growth: Develop team members’ skills, technical knowledge, and careers within Cloudflare, coaching future managers and technical leaders on leveraging automated AI workflows to eliminate manual overhead.

• Own Performance Metrics: Oversee and report on Canadian 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 Canadian 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 Canada 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 Canadian market.

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 Canadian regional 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).

What Makes Cloudflare Special?

We’re not just a highly ambitious, large-scale technology company. We’re a highly ambitious, large-scale technology company with a soul. Fundamental to our

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