Segment Leader, Mid-Market

About the position

Reporting into our Head of Sales, Checkout.com is actively looking for a passionate and results-oriented Sales Leader to help fuel the growth of our North American Sales team. 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. You will bring deep experience in Payments and/or the adjacent B2B technology space, adept at building lasting, high-value relationships with merchants and colleagues alike. The successful Leader must seamlessly transition between hands-on, deal-level detail and key strategic decision-making that scales our commercial capability and ensures alignment with our global vision.

Responsibilities

  • Recruit, build, lead, mentor, and energize a national commercial team to consistently surpass revenue targets by successfully selling Checkout.com’s product suite to North American lower Middle Market merchants.
  • Deliver the necessary structure, cadence, quality, and discipline to create a professionalized, scalable, and world-class commercial capability for the Middle Market segment.
  • 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.
  • 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.
  • 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.

Requirements

  • Strong track record of building, managing, and delivering exceptional results within a commercial team, ideally within a larger global organization.
  • 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.
  • An inspiring, engaging people leader and 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.
  • Experience operating in a high-growth, fast-paced environment. Able to cope with the ambiguity of scaling a team, sometimes with lean resources.
  • Possesses a strategic mindset combined with an ability to adopt a hands-on approach and be close to the detail when needed. Proven ability to translate a sales strategy into clear operational plans and repeatable processes that drive consistent execution across the team.

Benefits

  • Ownership
  • Fewer blockers
  • Work that makes a difference from day one
  • Ambition met with opportunity
  • Growth in your hands
  • Work as one team
  • Back each other to succeed
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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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