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Senior Enterprise Sales Executive at Checkout.com | Canada

Checkout.comHome-based, Canada (ON)
Remote Full-time

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Experience Level

Senior

Qualifications

Ideal candidates will possess a proven track record in enterprise sales, particularly within the fintech or payments landscape. Strong analytical skills, a proactive approach to market development, and the ability to build enduring relationships with clients are essential. You should be comfortable navigating complex sales processes and demonstrating a deep understanding of customer needs.

About the job

About Checkout.com

Checkout.com is a global fintech company powering online payments for brands like eBay, ASOS, Klarna, Uber Eats, and Sony. The platform supports billions of transactions each year, making digital payments simple and reliable for businesses and their customers.

With 19 offices across six continents and headquarters in London, Checkout.com combines a performance-driven culture with a commitment to ongoing improvement. The company is expanding in Canada and has become a direct acquirer in the region. 2026 will be a significant year for growth, and the team is building its Canadian presence starting in Toronto.

Role Overview: Senior Enterprise Sales Executive (Home-based, Canada - ON)

This is a founding role on the Canadian sales team. The Senior Enterprise Sales Executive will help shape Checkout.com's entry into the Canadian market, working with leading merchants and building the foundation for long-term success. The position blends the pace and ownership of a startup with the backing of a global payments leader.

What You Will Do

  • Strategic Prospecting: Identify and engage high-value Enterprise accounts within the assigned territory. Build a strong sales pipeline through market research, networking, and outreach.
  • Consultative Engagement: Collaborate with merchant leaders to understand their business needs and present tailored payment solutions that deliver value.

Location

This is a home-based position in Canada (Ontario).

Learn More

For more about the company, visit Checkout.com.

About Checkout.com

Checkout.com is a leading payment solutions provider, empowering businesses to thrive in a digital economy by streamlining financial transactions across the globe. Our mission is to make payments easy, reliable, and efficient, ensuring a seamless experience for both merchants and their customers.

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