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: Operate with urgency, persistence, and accountability—running territory like your own business. Strategic Acumen: Highly analytical and data‑driven, building smart hypotheses, using insights to guide prioritisation, and leveraging 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: Actively seek feedback, iterate quickly, and adapt 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 organised, strong at prioritising, 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: Sell a modern platform that already wins with sophisticated merchants—now 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 offering flexibility, with three days per week in the office to support collaboration and connection. #J-18808-Ljbffr