Senior Enterprise Sales Executive (Toronto)

Overview

Checkout.com is expanding into Canada and hiring founding Enterprise Sales Executives to establish and scale our presence in Toronto. 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, own the end-to-end new business sales cycle for Enterprise merchants across the Canadian market.
• 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 q...