Principal Customer Engineer, Central Majors - Toronto Canada

Available Location: Toronto, Canada

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. 

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.

What you will do as a Customer Engineer

The Customer Engineer (CE) is the core driver of our technical go-to-market strategy: a trusted technical advisor and primary architect of the customer journey. You will bridge the gap between technical strategy and business value—guiding enterprise clients from initial pre-sales technical validation through onboarding, deployment architecture, and full lifecycle expansion. Sitting within the GTM organization and reporting to a Customer Engineering Leader, you will not hand off your customers once an initial agreement is reached. Instead, you will operate as a quota-carrying technologist, leveraging AI-augmented workflows to eliminate administrative toil so you can focus on high-value architectural design and driving measurable business outcomes across the entire customer journey.

Key Responsibilities

• Technical Validation: Partner closely with Account Executives to lead technical deep-dive discovery, capture business requirements, and map complex customer infrastructure - DNS, CDN, Zero Trust, Network Security, Workers - to fit-for-purpose Cloudflare architectures and bespoke solutions. . Define, scope, success criteria, and technical evaluations plans for Proof of Concepts (PoCs) and Technical Validations. Deliver tailored technical presentations, architectural diagrams, and demonstrations that show how Cloudflare solves specific performance, security, and reliability challenges. Proactively address complex technical objections, security compliance questions, and edge-case architectural requirements during the sales cycle. Take accountability for a suitable solution deployment strategy (Customer, Partner or Cloudflare Professional services) being an integral part of all proposals.
• Customer Adoption & Value Realization: Provide oversight to technical onboarding and implementation, but not execute the implementation, serving as the primary executive and engineering contact for the customer. Design structured migration and onboarding blueprints tailored to the customer’s environment (e.g. DNS migrations, Zero Trust rollouts, WAF tuning guidance), and act as the lead consultant for customer engineering teams, walking them step-by-step through configuration best practices.  Partner with Account Executives to own discovery, demos, onboarding, technical health, risk, and expansion strategy. Proactively monitor customer health scores and telemetry to ensure rapid time-to-value, resolve integration bottlenecks, and reduce deployment risk.
• Commercial Accountability & Expansion: Carry a variable quota tied directly to new business acquisition and/or ongoing account growth. Be commercially accountable for ensuring deep platform adoption, retaining revenue, and identifying strategic cross-sell and up-sell opportunities based on product usage data. Lead technical Quarterly Business Reviews (QBRs) to translate platform capabilities into return on investment for C-level executives.
• Trusted Advisory: Act as a trusted technical advisor throughout the entire customer lifecycle, maintaining a continuous, deep relationship with key stakeholders from initial onboarding through maturity, renewal, and expansion. Provide thought partnership on architecture, AI control layers, security posture, and deployment confidence. Identify potential deployment risks or integration bottlenecks early, and provide remediation strategies to de-risk customer outcomes. 
• AI Orchestration & Workflow Automation: Leverage AI agents, Large Language Models (LLMs), and internal platforms to automate routine tasks such as RFP/Security Questionnaire responses, sandbox provisioning, basic telemetry monitoring, and internal/external documentation, reclaiming your time for strategic customer advisory.
• Education & Enablement: Partner closely with the Enablement Team to design, build, and govern technical resources. Define, document, and educate both internal teams and customers on deliverables such as Standard Operating Procedures (SOPs), architectural best practices, and technical guides to continuously raise the technical baseline across the organization.

Minimum Qualifications

• Experience: Experience in a customer-facing technical role, such as Solutions Engineering, Customer Engineering, Professional Services,  Sales Engineering, Technical Account Management, or as a Forward Deployed Engineer (years of experience required will vary based on Associate, Senior, Staff, or Principal leveling).
• Architectural Mindset: Ability to white-board, design, and articulate complex enterprise network and security architectures clearly.
• Consultative & Advisory Skills: Excellent communication skills with the ability to translate deeply technical concepts into business outcomes for both hands-on engineers and C-level executives.
• Commercial Mindset: Proven track record of operating in a quota-carrying or revenue-aligned environment, with a strong understanding of SaaS metrics, business value translation, and enterprise sales cycles.
• Communication: Exceptional presentation and stakeholder management skills, capable of bridging the gap between deep technical implementation details and high-level C-suite business strategy.
• Technical Breadth: We do not expect every candidate to be an expert in every domain. Qualified candidates will demonstrate depth in at least four of the technical areas below:
• Internet fundamentals: Deep understanding of how the Internet works, including OSI Model layers 1–7, BGP, GRE, TCP/UDP, DNS (authoritative and recursive), HTTP(S), and SSL/TLS.
• Security: Expertise in the security of Internet properties, including WAF, Bot Management, Firewalls, Rate Limiting, (M)TLS, Zero Trust, and SASE concepts.
• Performance: Expertise in the performance of Internet properties, including speed, latency, caching, video streaming, HTTP/2, and TLS 1.3.
• AI Proficiency: Familiarity with prompt engineering, AI-assisted scripting and log analysis, LLM utilization, and workflow automation to augment everyday CE workflows.
• Coding/Scripting: Proficiency in Python, JavaScript, Bash, Lua, Go, or similar languages to write custom integration scripts, API connectors, and edge computing functions.
• Developer Platform Fluency: Experience designing, building, deploying or scaling applications using RESTful/GraphQL APIs, SDKs, webhooks, and developer tooling in cloud-native environments. Familiarity with infrastructure-as-code (Terraform, Pulumi), CI/CD pipelines, and observability for developer-led deployments.

Strongly Preferred Qualifications (The "Good-to-Haves")

• Technical Enablement: Track record of creating and delivering technical enablement - workshops, code samples, documentation, or developer onboarding - that accelerates customer adoption of complex platforms. 
• Applied AI Knowledge: Experience with LLM orchestration, Retrieval-Augmented Generation (RAG) architectures, and model-access controls.
• Regulatory Knowledge: Understanding of regulatory requirements such as PCI DSS, HIPAA, and SOC 2.
• Hyperscaler / Digital Native Background: Talent coming out of hyperscalers, digital natives, distributed systems environments, or startups is strongly valued for its deeper cloud fluency and advanced architecture depth.

Education

Undergraduate or graduate degree in Computer Science, Engineering, or a related field. 

Travel

This role may require travel up to 20–50% to attend customer meetings, conferences, industry events, and in-person team collaboration.

Compensation

This role features a competitive base salary and a variable compensation structure tied directly to the successful execution of full-lifecycle commercial targets, including new business acquisition, ongoing adoption milestones, and overall account expansion.