Director, Customer Engineering

Responsibilities

• 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.
• Recruit, interview, and onboard new team members while managing overall capacity, equitable workload distribution, and optimizing team productivity through AI-driven operational tools.
• 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.
• 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.
• Swiftly identify and resolve regional issues by collaborating with global regional leads and deploying automated Customer Escalation AI Reviewers to streamline complex technical escalations.
• 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.
• 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.

Must-Have Skills

• 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.
• 8+ years of experience as a hands-on Customer Engineer or Technical Consultant delivering complex SaaS, PaaS, or cloud security solutions.
• Proven track record of successfully partnering with Account Executives, Customer Success teams, and executive-level stakeholders to drive enterprise revenue and successful customer outcomes.
• Demonstrable experience in successfully navigating, de-escalating, and solving complex technical escalations, utilizing automated escalation frameworks and cross-functional AI reviewer pipelines.
• Strong experience supporting enterprise contract management, commercial negotiations, compliance, or project management frameworks within the Canadian market.

Bonus Points

• Prior experience spanning financial consulting, software development, product management, or technical project delivery.
• Strong existing relationships or familiarity with major Canadian regional 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).