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Middle Market Sales Representative Jobs (NOW HIRING)

Checkout.com

Middle Market Sales Leader

New York, NY · On-site

$324K - $438K/yr

... 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 ...

Dawn Foods

Market Sales Rep II

Houston, TX · Remote

$61K - $101K/yr

Job Purpose and OverviewThe Market Sales Representative II (MSR II) is a field-traveling, customer-facing sales role responsible for driving profitable growth within a defined territory supported by ...

Dawn Foods

Market Sales Rep II

Houston, TX · On-site

Job Purpose and Overview The Market Sales Representative II (MSR II) is a field-traveling, customer-facing sales role responsible for driving profitable growth within a defined territory supported by ...

Dawn Foods

Market Sales Rep II

Dayton, OH · Remote

Job Purpose and Overview The Market Sales Representative II (MSR II) is a field-traveling, customer-facing sales role responsible for driving profitable growth within a defined territory supported by ...

Dawn Foods Ltd.

Market Sales Rep II

Houston, TX · On-site

Job Purpose and Overview The Market Sales Representative II (MSR II) is a field-traveling, customer-facing sales role responsible for driving profitable growth within a defined territory supported by ...

Cambria

Market Sales Representative

$78K - $104K/yr

Ensure market development to maximize sales within the market by developing quarterly and annual ... Sell Cambria by educating on and representing the brand and product * Present product knowledge ...

Ecolab Inc.

Market Sales Representative

Philadelphia, PA · On-site

$75K - $113K/yr

Join Ecolab's sales team as a Market Sales Representative in the Philadelphia market. Within our industry leading Institutional division, grow sales within an existing territory of accounts by ...

Ecolab

Market Sales Representative

Philadelphia, PA

$75K - $113K/yr

Join Ecolab's sales team as a Market Sales Representative in the Philadelphia market. Within our industry leading Institutional division, grow sales within an existing territory of accounts by ...

Authentic

Middle-Market Underwriter

Dayton, OH · On-site

We are seeking a motivated and analytical Middle Market GL Underwriter to join our growing team ... Partner closely with sales leadership to support business development and retention efforts

Northwest

Sr. Middle Market Banker - Healthcare

... Middle Market Banker - Healthcare is responsible for serving as a trusted business advisor to ... Participate in continued sales, product and credit training * Ensure compliance with Northwest ...

Truist

Middle Market Banking Leader - OH

Columbus, OH · On-site

Specific activities may change from time to time. 1. Serve as primary sales leader for team of ... The requirements listed below are representative of the knowledge, skill and/or ability required.

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Middle Market Sales Representative information

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$28.5K

$49.6K

$73.5K

How much do middle market sales representative jobs pay per year?

As of Sep 13, 2026, the average yearly pay for middle market sales representative in the United States is $49,611.00, according to ZipRecruiter salary data. Most workers in this role earn between $41,000.00 and $55,000.00 per year, depending on experience, location, and employer.

What is a middle market sales representative?

A Middle Market Sales Representative is a sales professional who focuses on selling products or services to mid-sized businesses, typically those that are larger than small businesses but smaller than large enterprises. Their responsibilities often include identifying potential clients, building relationships, understanding client needs, and closing sales deals. They may work across various industries and are key in driving revenue growth within the middle market segment. Strong communication, negotiation, and problem-solving skills are essential for success in this role.

What are the key skills and qualifications needed to thrive as a middle market sales representative?

To excel as a Middle Market Sales Representative, you need strong sales acumen, a solid understanding of business-to-business (B2B) sales processes, and preferably a bachelor's degree in business or a related field. Familiarity with CRM platforms like Salesforce, sales analytics tools, and industry-specific software is typically required. Outstanding communication, negotiation, and relationship-building skills help you stand out in this role. These abilities are vital for effectively managing complex sales cycles, building long-term client partnerships, and consistently meeting revenue targets.

What are some common challenges faced by middle market sales representatives, and how can they be addressed?

Middle Market Sales Representatives often encounter challenges such as navigating complex decision-making processes within client organizations and managing longer sales cycles. Building relationships with multiple stakeholders and understanding each company's unique needs is crucial to success. To address these challenges, it's important to maintain clear and consistent communication, leverage CRM tools to track opportunities, and collaborate closely with internal teams like product specialists and customer success managers. Proactively researching each prospect and preparing tailored solutions can also help build trust and accelerate deal closure.

What cities are hiring for Middle Market Sales Representative jobs?

Cities with the most Middle Market Sales Representative job openings:

What states have the most Middle Market Sales Representative jobs?

States with the most job openings for Middle Market Sales Representative jobs include:

What are popular job titles related to Middle Market Sales Representative jobs?

For Middle Market Sales Representative jobs, the most frequently searched job titles are:

Infographic showing various Middle Market Sales Representative job openings in the United States as of August 2026, with employment types broken down into 81% Full Time, 18% Part Time, and 1% Contract. Highlights an 77% Physical, 1% Hybrid, and 22% Remote job distribution, with an average salary of $49,611 per year, or $23.9 per hour.

Middle Market Sales Leader

New York, NY • On-site

Checkout.com
See more jobs at Checkout.comexternal

$324K - $438K/yr

Full-time

Posted 29 days ago

Job description

Company Description
We're Checkout.com. You might not know our name, but companies like eBay, Spotify, Klarna, Uber, and Sony do, because we're behind many of the digital experiences you use every day.
We are where the world checks out, enabling over 10 billion transactions yearly for more than one billion global shoppers.
Whether you want to book a holiday, order food, renew a subscription, or check out online, there's a good chance our tech powers the payments behind the scenes. Our platform helps the most ambitious businesses deliver effortless digital experiences, at scale.
If you want to do career-defining work, you've come to the right place. We move fast, think globally, and believe great teams are built by hiring exceptional people with conviction, curiosity, and the desire to make an impact.
With 20 offices across six continents and London as our HQ, we're shaping the future of fintech - and we're just getting started.
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.
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's 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.
Life at Checkout.com
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? Visit our Careers Page to learn more about our culture, open roles, and what drives us.
For a closer look at daily life at Checkout.com, follow us on LinkedIn and Instagram

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