Segment Leader, Mid-market

Checkout

North America
**
Recruit, build, and lead a national commercial team
Drive new opportunities into the pipeline
Deep experience in payments and/or b2b technology
** Checkout.com is seeking a Segment Leader for Mid-market to lead and build a national commercial team focused on the growth of their North American segment. The ideal candidate should have a strong background in payments technology and sales leadership, with a focus on recruiting and developing talent. **

Job Summary

  • 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.
  • Deliver the necessary structure, cadence, quality, and discipline to create a professionalized, scalable, and world-class commercial capability for the Middle Market segment.
  • We empower passionate problem-solvers to collaborate, innovate and do their best work.

Matching Summary

Match Score: 75

** Checkout.com is seeking a Segment Leader for Mid-market to lead and build a national commercial team focused on the growth of their North American segment. The ideal candidate should have a strong background in payments technology and sales leadership, with a focus on recruiting and developing talent. **

Skills & Requirements

Must-have

  • Recruit, build, and lead a national commercial team
  • Drive new opportunities into the pipeline
  • Deep experience in Payments and/or B2B technology
  • Build and nurture valuable relationships with decision-makers
  • Subject matter expert on North American payments

Nice-to-have

  • Inspiring, engaging people leader
  • Growth and scale-up mindset
  • Fast-moving, performance-obsessed culture

Key Requirements

  • Strong track record of building, managing, and delivering exceptional results
  • Deep knowledge and understanding of payments technology and the Middle Market or Enterprise ecosystems
  • Experience operating in a high-growth, fast-paced environment
  • Proven ability to translate a sales strategy into clear operational plans

Work Rights

Not specified

Tailored Resume

Cover Letter