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Checkout.com is seeking a Segment Leader to build and lead a national commercial sales team focused on the high-growth North American mid-market segment. Reporting to the Head of Sales, you will own the full P&L for this critical business unit, responsible for recruiting, developing, and scaling a world-class sales organization that consistently exceeds revenue targets.
Key responsibilities include: recruiting and mentoring a national commercial team to sell Checkout.com's payment solutions to mid-market merchants; establishing the operational structure, cadence, and discipline needed for a scalable, professionalized sales capability; driving pipeline generation through alignment with marketing, partnerships, and solutions engineering; actively coaching deals and building relationships with founders and senior decision-makers; and serving as a strategic partner across product, technology, and implementation teams to optimize processes.
You will bring deep expertise in payments technology and B2B SaaS sales, with a proven track record of building and managing high-performing commercial teams in larger global organizations. You must understand the competitive payments landscape, mid-market or enterprise ecosystems, and what defines a stellar payments partner. Strong people leadership skills are essential—you'll spend significant time recruiting and developing top talent in a high-growth, fast-paced environment. You combine strategic thinking with hands-on execution, translating sales strategy into clear operational plans and repeatable processes.
Checkout.com powers over 10 billion transactions yearly for more than one billion global shoppers, serving companies like eBay, Spotify, Klarna, Uber, and Sony. With 20 offices across six continents and London as headquarters, the company is shaping the future of fintech. The role offers hybrid flexibility (three days per week in office) and the opportunity to make a career-defining impact in a fast-moving, ambitious organization.
