National Sales Director, Major and Federal Accounts in Toronto

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.

Available Locations: Toronto, Ontario

About the Department

The Field Sales department is responsible for direct revenue generation through the acquisition of new enterprise clients and the expansion of existing high-value accounts. Utilizing a modern, digital-first, AI-supported sales model, our team eliminates manual administrative overhead to focus on high-impact strategic engagement, helping enterprise and public sector customers solve critical security and performance challenges.

What you’ll do

We are looking for an experienced Sales Leader to lead and grow the business in Canada with responsibility for driving Cloudflare’s revenue and brand awareness in the region. Based in the Greater Toronto Area, the Sales Leader will require both strategic and hands-on leadership skills to drive a modernized go-to-market strategy, including hiring, leading, and growing the sales team, optimizing AI-supported pipeline engines, and closing complex transactions to scale the region.

Additional responsibilities will include:

• Design, build, and execute regional strategies in collaboration with regional and global functional leaders, leveraging data-driven automation to maximize team productivity.
• Lead and grow the Canada Major Accounts and Federal sales team, fostering an environment of AI-native curiosity, high performance, and continuous iteration.
• Serve as the local executive point of contact for all Major Account & Federal functions in Canada, driving strategic partner alignment and executive customer relationships.
• Drive a modern business cadence for forecast calls, deal reviews, customer account reviews, and weekly team meetings by utilizing automated account metrics and pipeline insights.
• Lead cross-functional programs and campaigns—working across sales, marketing, customer success, solutions engineering, and channel partners—to convert high-intent market signals into closed revenue.
• Drive regional sales growth through organizational planning, high-touch executive engagement, and outstanding execution of digital-first go-to-market strategies.
• Represent Cloudflare as the single point of contact for Regional operational concerns, ensuring proper escalation and resolution.
• Ensure corporate policy and regulatory initiatives (including public sector and federal standards) are consistently applied and followed across the team.
• Inspire interpersonal effectiveness, develop top-tier sales talent, and lead teams through evolving technological landscapes.
• Act as an active “doer” and “influencer,” representing Cloudflare at key external conferences, media opportunities, and PR events.

Examples of desirable skills, knowledge and experience:

• Currently in a sales leadership role; Bachelor’s degree required.
• 10+ years of SaaS sales experience, selling to large enterprise accounts in both the Private and Federal sectors.
• 5+ years of SaaS cybersecurity/networking sales management experience leading a named field sales team.
• Proven experience managing and coaching long, complex, high-value enterprise sales cycles, with a track record of driving partner-led revenue.
• Demonstrated experience selling into top-tier key verticals including Financial Services, Public Sector, Service Providers, Retail, Manufacturing, Energy, and Media.
• Solid technical grounding in IaaS, Networking, and Information Security services, with an aptitude for continuously learning modern technical architecture.
• Familiarity with AI-assisted sales tools, automated pipeline workflows, and digital-first go-to-market methodologies that minimize manual administrative friction.
• Exceptional leadership, executive presentation, and cross-functional communication skills.
• Self-motivated, entrepreneurial mindset with a passion for problem-solving and innovation.
• Comfortable working in a fast-paced, dynamic environment, including working in an office environment in the Greater Toronto Area (GTA) 2–3 times a week.

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

Please note that applicants who progress to the offer stage of the interview process may be asked to attend an in-person interview within one of the Cloudflare Offices or Cloudflare Hubs. More details about this will be available at that stage of the interview process.

This position may require access to information protected under U.S. export control laws, including the U.S. Export Administration Regulations. Please note that any offer of employment may be conditioned on your authorization to receive software or technology controlled under these U.S. export laws without sponsorship for an export license.

Cloudflare is proud to be an equal opportunity employer. We are committed to providing equal employment opportunity for all people and place great value in both diversity and inclusiveness.