Head of Sales, Canada

Gradial · Remote - Canada · Remote

Posted 7/24/2026 · last confirmed live 8/26/2026

Gradial is the marketing operations system of work that helps marketers and creatives move from idea to execution faster. Our platform orchestrates across martech stacks, workflows, and people to automate marketing execution, cutting execution time, so marketers focus on the work only humans can do: shaping brands, understanding customers, and creating the work that moves people. Backed by leading investors, we’re building software that adapts to the user, not the other way around. We move with urgency, operate with ownership, and solve hard problems from first principles. If you want to do ambitious work, take real responsibility, and help define the future of AI-native content operations, you’ll do your best work here. The Role   Gradial is hiring a Head of Sales, Canada to build our Canadian business from the ground up. As one of our first employees in Canada, you’ll lead the pursuit of net new enterprise and strategic customers while establishing Gradial as a trusted partner to Canada’s leading marketing organizations.   This role combines direct selling with broader market development. You’ll work closely with marketing executives, marketing technology leaders and other senior stakeholders to introduce Gradial, uncover high-value use cases and guide complex organizations through the buying process.   You’ll report to the CRO and begin as a senior individual contributor. As demand grows, you’ll define the structure of the Canadian sales organization and hire the team needed to expand our reach.   What You’ll Own   Define and execute Gradial’s sales strategy for the Canadian market   Create net new pipeline across enterprise and strategic accounts   Lead customer conversations with senior marketing, digital and marketing technology executives   Manage complex opportunities from initial discovery through commercial close   Build account plans that connect Gradial’s platform to measurable customer priorities   Partner with US sales leaders to support Canadian expansion within existing global accounts   Develop Gradial’s presence through customer relationships, market insight and industry engagement   Collaborate with Marketing to shape regional campaigns, events and account-based programs   Share customer and market feedback with Product and leadership to inform company strategy   Design and grow the Canadian sales team as the region develops   What We Need   12+ years of progressive experience in enterprise technology sales   Demonstrated success generating and closing net new business with large, complex organizations   Experience selling SaaS, marketing technology or digital transformation solutions   Strong relationships across the Canadian enterprise and marketing technology community   Credibility with VP and C-suite buyers across Marketing, Digital and Technology   Experience building a market, territory or sales function from an early stage   Strong commercial judgment and the ability to create momentum without a mature regional playbook   Ability to communicate the value of AI-powered technology in practical business terms   A collaborative approach to working across Sales, Marketing, Product and Customer teams   Motivation to remain hands-on while building toward a formal leadership role   Nice to Have   Experience selling AI products into enterprise marketing organizations   Experience building or leading an early-stage regional sales team   Professional fluency in French   What we offer Performance-based annual bonus Meaningful equity awards Medical, dental & vision (fully covered for employees with 75% for dependents) Fertility & family-planning support 401k plan Unlimited PTO A beautiful Seattle office with a gym, sauna, and bike parking Free lunch three days a week in our HQ A front-row seat to building category-defining AI infrastructure You'll thrive here if you Learn quickly, actively seek out new challenges, and regularly reconsider “how it’s always been done.” Want to have real impact with zero bureaucracy. Have an innate drive for being 1% better than the day before, building towards greatness. Embrace AI as a core tool for problem-solving, innovation, and scale. Show customer-obsession (internal or external), high ownership/accountability, and bias for action. Communicate clearly, directly, with curiosity, and assuming good intentions. Thrive in fast-paced, hyper-growth environments where building better > maintaining status quo. AI Literacy & Interviewing Tools As an AI-first company, we prioritize AI literacy as a core competency in our hiring decisions. We’re excited by candidates who thoughtfully apply AI tools in their work, but during interviews we’re focused on you. This is your opportunity to show how you think, communicate, and solve problems. Over-reliance on AI-generated responses during the interview process (especially when it obscures your own voice) will result in disqualification. We want to understand your unique perspective and how you approach challenges, both with and without AI. Gradial is dedicated to creating an environment where diverse perspectives are valued and all team members can grow. We offer competitive compensation, equity, flexible work hours, comprehensive benefits, and a collaborative culture focused on learning and impact.

This role is published by Gradial on greenhouse. SwiftFit is not the employer and does not accept applications.