[Hiring] Director, Customer Engineering @Cloudflare

Role Description

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
• Team effectiveness across the entire Canadian portfolio

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.

Qualifications

• 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).

Benefits

• 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 mission to help build a better Internet is protecting the free and open Internet.

Company Description

• Project Galileo: Since 2014, we've equipped more than 2,400 journalism and civil society organizations in 111 countries with powerful tools to defend themselves against attacks that would otherwise censor their work.
• Athenian Project: In 2017, we created the Athenian Project to ensure that state and local governments have the highest level of protection and reliability for free.
• 1.1.1.1: We 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.