Middle Market Sales Leader

Segment Ownership & Scaling

• Recruit, build, lead, mentor, and energize a commercial team to consistently surpass revenue targets by successfully selling Checkout.com’s product suite to North American lower Middle Market merchants

World-Class Commercial Engine

• Deliver the necessary structure, cadence, quality, and discipline to create a professionalized, scalable, and world-class commercial capability for the Middle Market segment

Pipeline Generation

• Work with the team to help drive new opportunities in our target Ideal Client Profile (ICP) and Strategic Territory Planning (STP) into the pipeline
• 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

Pipeline Acceleration

• 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

Strategic Cross-Functional Partner

• 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

Required Qualifications

• Commercial Sales Success: Strong track record of delivering exceptional sales results within a commercial team, ideally within a larger global organization
• Payments & Segment Expertise: 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
• Visionary People Leadership: An inspiring and engaging 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
• Growth & Scale-Up Mindset: Experience operating in a high-growth, fast-paced environment. Able to cope with the ambiguity of scaling a team, sometimes with lean resources
• Strategic Execution: Possesses a strategic mindset combined with an ability to adopt a hands-on approach and be close to the detail when needed. Demonstrates ability to translate a sales strategy into clear operational plans and repeatable processes that drive consistent execution across the team