Checkout.com
Middle Market Sales Leader
$324K–$439K
New York · Hybrid · Full-time · Posted Aug 31, 2026
About the job
Leads the recruitment and management of Checkout.com’s North American lower Middle Market sales team, scaling its commercial operation and driving merchant revenue growth.
What you'll do
- Recruit, develop, and lead a commercial team to exceed revenue targets selling Checkout.com’s product suite to lower Middle Market merchants.
- Build scalable sales structures and processes, and work with Marketing, Partnerships, and Sales to generate and accelerate pipeline.
- Coach key deals and partner across teams to improve sales and onboarding processes.
What they ask for
- Strong track record of commercial sales results.
- Deep knowledge of payments technology and the Middle Market or Enterprise ecosystem, including the competitive payments landscape.
- Experience attracting, recruiting, managing, and developing commercial talent.
- Experience in a high-growth, fast-paced environment and ability to translate sales strategy into operational plans and repeatable processes.
Pay
$324.2K – $438.6K (pay type not stated; currency code not stated)
Model-written summary · the original posting is authoritative