Senior Enterprise Sales Executive

Company Description We’re Checkout.com – you might not know our name, but companies like eBay, ASOS, Klarna, Uber Eats, and Sony do. That moment when you check out online? We make it happen. Checkout.com is where the world checks out. Our global network powers billions of transactions every year, making money move without making a fuss. We spent years perfecting a service most people will never notice. Because when digital payments just work, businesses grow, customers stay, and no one stops to think about why. With 19 offices spanning six continents, we feel at home everywhere – but London is our HQ. Wherever our people work their magic, they’re fast-moving, performance-obsessed, and driven by being better every day. Ideal. Because a role here isn’t just another job; it’s a career-defining opportunity to build the future of fintech. Job Description Are you looking for an opportunity to shape a new market from the ground up at one of the world’s fastest-growing fintechs? At Checkout.com, we power payments for some of the world’s most innovative brands; Klarna, Sony, eBay, and thousands more through a modern, unified platform trusted globally. We are now expanding into Canada in a major way. Checkout.com has recently become a direct acquirer in Canada, and 2026 marks a strategic inflection point for our business in the region. To build on our global performance and unlock the next phase of growth, we are hiring founding Enterprise Sales Executives to establish and scale our presence in Toronto. As part of this early team, you will play a defining role in shaping our go-to-market motion, winning flagship Canadian merchants, and building the foundation for Checkout.com’s long-term success in the market. This is a rare chance to join a hyper-growth fintech at a pivotal moment—combining startup-like ownership with the backing of a global category leader. What you will do: As a founding Enterprise Sales Executive for Canada, you will own the end-to-end new business sales cycle for Enterprise merchants across the Canadian market. You will: Strategically prospect and plan within a defined territory of high-value Enterprise accounts—leveraging market intelligence, networks, and disciplined outbound execution to build a robust pipeline. Engage consultatively with merchant leaders , deeply understanding their payments, risk, and operational challenges to propose tailored, high-impact solutions. Act as deal captain : coordinate cross-functional resources (performance, solutions engineering, risk, legal), build quantitative business cases, and drive opportunities forward with clear, strategic leadership. Lead complex negotiations , manage objections, and consistently bring high-value, multi-product deals to closure. Operate with ownership : track and analyze performance metrics, continuously refine strategy, and help shape our local GTM playbook. Represent Checkout.com in-market , helping to raise our profile, develop merchant relationships, and contribute insights to our global teams. Core Competencies: We’re looking for top sales athletes who thrive in high-growth, entrepreneurial environments and want to help build something meaningful in Canada: Entrepreneurial Drive: You operate with urgency, persistence, and accountability—running your territory like your own business. Strategic Acumen: Highly analytical and data-driven; you build smart hypotheses, use insights to guide prioritization, and leverage new technologies (including AI) to accelerate performance. Deal Leadership: Strong executive presence and comfort leading complex, multistakeholder Enterprise deals with C-suite engagement. Learning Mindset: You actively seek feedback, iterate quickly, and adapt your strategy based on results and evolving conditions. Relationship Building: Exceptional ability to build trust with senior merchant stakeholders and nurture long-term partnerships. Operational Excellence: Highly organized, strong at prioritizing, and effec ... (truncated, view full listing at source)