Who you are

- 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 the job involves

- 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

- 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

- 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 setting 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

Benefits

- Competitive pay: We offer a competitive total rewards package, where every employee is an owner of our stock.

- Take-what-you-need vacation: We encourage employees to find a comfortable work-life balance by taking as many days off as they need while still being able to perform their jobs satisfactorily. (We really mean it!)

- Paid maternity & paternity leave: Our global parental leave policy allows up to sixteen paid weeks of bonding leave time for all qualifying new parents.

- Employee benefits: We offer a comprehensive benefits package including healthcare, life insurance, short- and long-term disability, pension plans in accordance with the market practice in our locations.

- Commuter program: We are flexible about where we work and value connecting at the office. Our commuter benefits program is in place to support team members' commute to work via public transportation without the extra cost burden.

- Wellbeing: Global offerings that provide mental health, childcare and family forming support to our employees across our offices.

📌 National Sales Director (Toronto)
🏢 Cloudflare
📍 Toronto