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. At Cloudflare, 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. 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. Segmented by account complexity and size, the team works alongside Business Development, Solution Engineering, Customer Success, and Sales Operations to secure Cloudflare's people, processes, and technologies. 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. In this role, you will work actively with prospects, major enterprise customers, public sector accounts, and strategic partners to build 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. 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. Sound like something you’d like to be a part of? We’d love to hear from you! 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. All qualified applicants will be considered for employment without regard to their, or any other person's, perceived or actual race, color, religion, sex, gender, gender identity, gender expression, sexual orientation, national origin, ancestry, citizenship, age, physical or mental disability, medical condition, family care status, or any other basis protected by law. We are an AA/Veterans/Disabled Employer. Cloudflare provides reasonable accommodations to qualified individuals with disabilities. Please tell us if you require a reasonable accommodation to apply for a job. Examples of reasonable accommodations include, but are not limited to, changing the application process, providing documents in an alternate format, using a sign language interpreter, or using specialized equipment. If you require a reasonable accommodation to apply for a job, please contact us via e-mail at hr@cloudflare.com or via mail at 101 Townsend St. San Francisco, CA 94107.