Middle Market Sales Leader

How You'll Ignite Impact (Key Responsibilities)

• Segment Ownership & Scaling: Recruit, build, lead, mentor, and energize a commercial team to consistently surpass revenue targets by successfully selling Checkout.com 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. 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.
• 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

The High-Performance Profile

• 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.

• 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.
• 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?