Middle Market Sales Leader

About the role

Reporting into the Head of Sales, Checkout.com is actively looking for a passionate and results‑oriented Sales Leader to help fuel the growth of its North American sales team. This high‑impact role will recruit, build, and lead a national commercial team focused on the high‑growth Middle Market segment.

Key responsibilities

• Segment Ownership & Scaling – recruit, build, mentor and energize a commercial team to consistently exceed revenue targets with North American lower Middle Market merchants.
• World‑Class Commercial Engine – establish structure, cadence, quality and discipline to create a scalable, professional commercial capability for the segment.
• Pipeline Generation – drive new opportunities in the Ideal Client Profile and Strategic Territory Planning, aligning marketing, partnerships and sales to generate strong leads.
• Pipeline Acceleration – actively engage on key deals, provide strategic guidance, coaching and direct support to move opportunities efficiently through sales and onboarding.
• Strategic Cross‑Functional Partner – act as a subject‑matter expert on North American payments, collaborating with Marketing, Solutions Engineering, Product, Technology and Implementation teams.

Required profile

• Commercial Sales Success – proven track record of delivering exceptional sales results within a commercial team, preferably in a global organization.
• Payments & Segment Expertise – deep knowledge of payments technology and the Middle Market or Enterprise ecosystems, including competitive landscape.
• Visionary People Leadership – inspiring communicator with a passion for attracting, recruiting, managing and developing top commercial talent.
• Growth & Scale‑Up Mindset – experience thriving in high‑growth, fast‑paced environments and scaling teams with limited resources.
• Strategic Execution – ability to translate sales strategy into clear operational plans, repeatable processes and consistent execution.