Senior Enterprise Sales Executive - #225956

Company Description

We’re Checkout.com. You might not know our name, but companies like eBay, Spotify, Klarna, Uber, and Sony do, because we’re behind many of the digital experiences you use every day.

We are where the world checks out, enabling over 10 billion transactions daily for more than one billion global shoppers.

Whether you want to book a holiday, order food, renew a subscription, or check out online, there’s a good chance our tech powers the payments behind the scenes. Our platform helps the most ambitious businesses deliver effortless digital experiences, at scale.

If you want to do career-defining work, you’ve come to the right place. We move fast, think globally, and believe great teams are built by hiring exceptional people with conviction, curiosity, and the desire to make an impact.

With 20 offices across six continents and London as our HQ, we’re shaping the future of fintech – and we’re just getting started.

Are you looking for an opportunity to shape a new market from the ground up at one of the world’s fastest-growing fintechs? At Checkout.com, we power payments for some of the world’s most innovative brands; Klarna, Sony, eBay, and thousands more through a modern, unified platform trusted globally.

We are now expanding into Canada in a major way. Checkout.com has recently become a direct acquirer in Canada, and 2026 marks a strategic inflection point for our business in the region. To build on our global performance and unlock the next phase of growth, 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

As a founding Enterprise Sales Executive for Canada, you will own the end-to-end new business sales cycle for Enterprise merchants across the Canadian market. You will:

• 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

We’re looking for top sales athletes who thrive in high-growth, entrepreneurial environments and want to help build something meaningful in Canada:

• Entrepreneurial Drive: You operate with urgency, persistence, and accountability—running your territory like your own business.
• Strategic Acumen: Highly analytical and data-driven; you build smart hypotheses, use insights to guide prioritization, and leverage 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: You actively seek feedback, iterate quickly, and adapt your 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 organized, strong at prioritizing, 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: You’ll be selling a modern platform that already wins with some of the world’s most sophisticated merchants—now finally enabled for true local performance in Canada.
• Career-defining opportunity: Outstanding performers will have significant room for advancement as the Canada organization scales.
  
  

Additional Information

Bring all of you to work

We create the conditions for high performers to thrive, through real ownership, fewer blockers, and work that makes a difference from day one.

Here, you’ll move fast, take on meaningful challenges, and be recognized for the impact you deliver. It’s a place where ambition gets met with opportunity, and where your growth is in your hands.

We work as one team, and we back each other to succeed. So whatever your background or identity, if you’re ready to grow and make a difference, you’ll be right at home here.

It’s important we set you up for success and make our process as accessible as possible. So let us know in your application, or tell your recruiter directly, if you need anything to make your experience or working environment more comfortable.

Life at Checkout.com

We understand that work is just one part of your life. Our hybrid working model offers flexibility, with three days per week in the office to support collaboration and connection.

Curious about what it’s like to be part of our team? Visit our Careers Page to learn more about our culture, open roles, and what drives us.

For a closer look at daily life at Checkout.com, follow us on LinkedIn and Instagram