Outside Sales Representative / Field Sales ( B2B )

System One
Chicago, IL

Job Title: Outside Sales Representative / Field Sales ( B2B )

Location: Chicago, Illinois

Type: Direct Hire

For immediate consideration, please connect with me on LinkedIn at and then email your resume, work authorization status, current location, availability, and compensation expectations directly to [email protected] - make sure to include the exact job title and job location in your email message

*** Direct hire permanent full-time position with full benefits, including 401(k) plan with employer matching. Join a big, publicly traded, company with over $10 billion in annual global sales volume.


*** We are seeking a candidate for B2B outside (field) + outbound sales role to WORK WITH SMALL BUSINESSES. This role does NOT involve mid-market or enterprise clients = SHORT sales cycles. It is primarily OUTSIDE & OUTBOUND - rather than inside or inbound - sales, requiring frequent in-person, on-site visits to meet business owners or to attend locations where they can be reached, such as restaurant supply depots, etc.

B2B Sales Representative / Account Manager ( Sales Manager, Sales Executive, Account Executive , Field Sales, Outside Sales, Outbound Sales ) :

- Engage with small business owners, for example : retail merchants, restaurant owners, consumer service providers, etc - to offer customized Point-of-Sale (POS) / payment processing solutions.

- Travel throughout your assigned territory, collaborating with financial institutions to offer cutting-edge POS / payment processing solutions to clients. Generate your own leads and grow your book of business through outbound efforts and strategic networking

Required Qualifications (Skills, Experience) :

- Sales experience in a quota-driven environment working with small business clients. Field Sales / Outside Sales experience is a plus. Experience with face-to-face meetings, cold calling, prospecting, and independent lead generation.

- The key requirement for candidates is proven experience in direct sales - specifically conducting face-to-face meetings / in-person presentations with owners and decision-makers to sell products and/or services to small businesses that serve various consumer markets.

For immediate consideration, please connect with me on LinkedIn at and then email your resume, work authorization status, current location, availability, and compensation expectations directly to [email protected] - make sure to include the exact job title and job location in your email message .

System One, and its subsidiaries including Joulé, ALTA IT Services, and Mountain Ltd., are leaders in delivering outsourced services and workforce solutions across North America. We help clients get work done more efficiently and economically, without compromising quality. System One not only serves as a valued partner for our clients, but we offer eligible employees health and welfare benefits coverage options including medical, dental, vision, spending accounts, life insurance, voluntary plans, as well as participation in a 401(k) plan.

System One is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, age, national origin, disability, family care or medical leave status, genetic information, veteran status, marital status, or any other characteristic protected by applicable federal, state, or local law.

#M1
#LI-DP1

Ref: #404-IT Pittsburgh


System One, and its subsidiaries including Joulé, ALTA IT Services, TeamPeople, and Mountain Ltd., are leaders in delivering outsourced services and workforce solutions across North America. We help clients get work done more efficiently and economically, without compromising quality. System One not only serves as a valued partner for our clients, but we offer eligible employees health and welfare benefits coverage options including medical, dental, vision, spending accounts, life insurance, voluntary plans, as well as participation in a 401(k) plan.

System One is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, age, national origin, disability, family care or medical leave status, genetic information, veteran status, marital status, or any other characteristic protected by applicable federal, state, or local law.

Posted 2025-09-26

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