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), buil...