Segment Leader, Mid-Market
About the position
Reporting into our Head of Sales, Checkout.com is actively looking for a passionate and results-oriented Sales Leader to help fuel the growth of our North American Sales team. This role is an unique, high-impact opportunity to recruit, build, and lead a national commercial team focused entirely on the high-growth Middle Market segment—a critical engine for Checkout.com’s corporate strategy. You will bring deep experience in Payments and/or the adjacent B2B technology space, adept at building lasting, high-value relationships with merchants and colleagues alike. The successful Leader must seamlessly transition between hands-on, deal-level detail and key strategic decision-making that scales our commercial capability and ensures alignment with our global vision.
Responsibilities
- Recruit, build, lead, mentor, and energize a national commercial team to consistently surpass revenue targets by successfully selling Checkout.com’s product suite to North American lower Middle Market merchants.
- Deliver the necessary structure, cadence, quality, and discipline to create a professionalized, scalable, and world-class commercial capability for the Middle Market segment.
- Work with the team to help drive new opportunities in our target Ideal Client Profile (ICP) and Strategic Territory Planning (STP) into the pipeline. Additionally, work in close partnership with the wider Commercial team to align Marketing, Partnerships, and Sales in generating strong leads, driving engagement, and accelerating deal volume within the segment.
- Actively engage on key opportunities, offering strategic guidance, deal coaching and direct support to help the team progress deals efficiently through the sales and onboarding process. Help build and nurture valuable relationships with founders, senior leaders, and decision-makers in businesses, demonstrating strong financial acumen and a data-driven approach to achieving performance metrics.
- Serve as a subject matter expert on North American payments and the wider ecosystem. Work closely across Marketing, Solutions Engineering, Product, Technology, and Implementation teams to optimize processes and productivity.
Requirements
- Strong track record of building, managing, and delivering exceptional results within a commercial team, ideally within a larger global organization.
- Deep knowledge and understanding of both payments technology and the Middle Market or Enterprise ecosystems. Must understand the competitive payments landscape and what defines a stellar payments partner.
- An inspiring, engaging people leader and communicator with a passion in attracting, recruiting, managing, and developing top commercial talent. Must be ready to spend the first year recruiting and developing top talent.
- Experience operating in a high-growth, fast-paced environment. Able to cope with the ambiguity of scaling a team, sometimes with lean resources.
- Possesses a strategic mindset combined with an ability to adopt a hands-on approach and be close to the detail when needed. Proven ability to translate a sales strategy into clear operational plans and repeatable processes that drive consistent execution across the team.
Benefits
- Ownership
- Fewer blockers
- Work that makes a difference from day one
- Ambition met with opportunity
- Growth in your hands
- Work as one team
- Back each other to succeed
