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 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 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, multi‑stakeholder 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 effective at managing large deal cycles with multiple moving parts. Communication: Clear, compelling written and verbal communication skills. What Makes This Role Unique Founding market team: Shape the GTM motion, culture, and strategy for Canada from day one. High‑impact market: Canada is a top strategic priority for Checkout.com globally in 2026 and beyond. Best‑in‑class product + new local acquiring capabilities: You’ll be selling a modern platform that already wins with some of the world’s most sophisticated merchants—now finally enabled for true local performance in Canada. Career‑defining opportunity: Outstanding performers will have significant room for advancement as the Canada organization scales. Benefits Hybrid working model offers flexibility, with three days per week in the office to support collaboration and connection. #J-18808-Ljbffr