Senior Enterprise Sales Executive (Fintech)

TL;DR

Senior Enterprise Sales Executive (Fintech): Driving the market entry and scaling of payment solutions in Canada with an accent on winning flagship enterprise merchants and establishing a local go-to-market motion. Focus on building a robust pipeline, leading complex multi-stakeholder negotiations, and shaping the foundation for long-term growth in the region.

Location: Must be based in Canada (Ontario) with a hybrid work model (3 days/week in office).

Company

Checkout.com is a global fintech leader powering digital payments for innovative brands like Klarna, Sony, and eBay through a modern, unified platform.

What you will do

• Own the end-to-end new business sales cycle for high-value enterprise merchants in the Canadian market.
• Strategically prospect and plan within a defined territory to build a robust sales pipeline.
• Engage consultatively with merchant leaders to propose tailored payment and risk solutions.
• Act as deal captain by coordinating cross-functional teams including performance, solutions engineering, and legal.
• Lead complex negotiations and drive multi-product deals to closure.
• Represent the company in-market to raise brand profile and develop long-term merchant relationships.

Requirements

• Must be based in Canada (Ontario) and able to work in a hybrid capacity.
• Proven track record in enterprise sales, ideally within fintech or high-growth technology sectors.
• Strong executive presence with experience leading complex, multi-stakeholder deals at the C-suite level.
• Analytical and data-driven approach to territory management and strategy.
• Exceptional communication and relationship-building skills.
• Entrepreneurial mindset with the ability to operate with urgency and accountability.

Culture & Benefits

• Opportunity to join a founding market team and shape the local GTM strategy.
• Hybrid working model with three days per week in the office to foster collaboration.
• Career-defining opportunity to scale a business in a top strategic global market.
• Fast-paced, performance-obsessed environment with a focus on ownership and impact.