Director, Customer Engineering

Cloudflare • Toronto, ON

18h • Remote

About The Position

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.

Requirements

• 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.

Nice To Haves

• 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).

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.

Benefits

• 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, technology already used by Cloudflare’s enterprise customers--at no cost.
• 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, so that their constituents have access to election information and voter registration. Since the project, we've provided services to more than 425 local government election websites in 33 states.
• 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. This is available publicly for everyone to use - it is the first consumer-focused service Cloudflare has ever released. Here’s the deal - we don’t store client IP addresses never, ever. We will continue to abide by our privacy commitment and ensure that no user data is sold to advertisers or used to target consumers.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed