Outside Sales Representative
The Middle Six, Chicago, IL, United States
Outside Sales Representative (Hybrid | Chicagoland Area)
Locations: Alsip & Addison, IL
Our client is an established locally owned company in the truck equipment industry with deep roots in the Chicagoland market. They are known for delivering high-quality solutions to contractors, municipalities, and fleet operators. They’re looking for an
Outside Sales Representative
early in their sales career who’s wired to compete, resourceful, and motivated by results. This isn’t a sit-back-and-wait role—it’s for a self-starter who doesn’t wait for direction, isn’t afraid to take risks, and knows how to turn conversations into real business. If you’re someone who figures things out, pushes through challenges, and thrives in a fast-moving environment—you’ll fit right in.
What You’ll Do You’ll be responsible for generating new business and growing relationships across a diverse customer base including contractors, municipalities, and fleet operators.
Prospect and develop new business through calls, emails, site visits, networking, and creative outreach
Build and maintain a strong, active sales pipeline
Manage daily activity and opportunities within a CRM platform (HubSpot experience is a plus)
Meet with customers on-site to understand their needs and recommend solutions
Partner with internal sales support who support quoting so you can stay focused on selling
Continuously learn the product line and industry to better serve your customers
What We’re Looking For
1–2 years of experience in retail sales, outside sales, or customer-facing roles
A “hunter” mentality—self-motivated, persistent, and not afraid of rejection
Strong communication skills and a natural ability to build relationships
Organized with an understanding of sales pipelines and CRM tools
Comfortable working in a fast-paced, ever-changing environment
Someone who takes initiative, figures things out, and follows through
Ability to stay focused on results, not just activity
Work Monday-Friday 8-5, flexible as needed for client and prospect engagement
Willingness to learn quickly and adapt
What Success Looks Like
Consistently generating new opportunities and building your pipeline
Staying active across multiple outreach channels
Converting conversations into revenue
Maintaining organization and accountability in your CRM
Meeting and exceeding sales goals
What You’ll Love About This Role
Hybrid flexibility (in-office up to 2x/week when not in the field)
Company vehicle provided
Base salary + uncapped commission (1.5% of revenue)
Ability to manage your territory and approach
A fast-moving environment where no two days are the same
You’ll have access to The Middle Six for sales coaching if needed
Requirements
Valid Driver's license
Drug test and background check
Must reside within reasonable driving distance to Alsip and/or Addison IL
The Middle Six is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, genetics, disability, age, veteran status, or any other characteristic protected by law.
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Locations: Alsip & Addison, IL
Our client is an established locally owned company in the truck equipment industry with deep roots in the Chicagoland market. They are known for delivering high-quality solutions to contractors, municipalities, and fleet operators. They’re looking for an
Outside Sales Representative
early in their sales career who’s wired to compete, resourceful, and motivated by results. This isn’t a sit-back-and-wait role—it’s for a self-starter who doesn’t wait for direction, isn’t afraid to take risks, and knows how to turn conversations into real business. If you’re someone who figures things out, pushes through challenges, and thrives in a fast-moving environment—you’ll fit right in.
What You’ll Do You’ll be responsible for generating new business and growing relationships across a diverse customer base including contractors, municipalities, and fleet operators.
Prospect and develop new business through calls, emails, site visits, networking, and creative outreach
Build and maintain a strong, active sales pipeline
Manage daily activity and opportunities within a CRM platform (HubSpot experience is a plus)
Meet with customers on-site to understand their needs and recommend solutions
Partner with internal sales support who support quoting so you can stay focused on selling
Continuously learn the product line and industry to better serve your customers
What We’re Looking For
1–2 years of experience in retail sales, outside sales, or customer-facing roles
A “hunter” mentality—self-motivated, persistent, and not afraid of rejection
Strong communication skills and a natural ability to build relationships
Organized with an understanding of sales pipelines and CRM tools
Comfortable working in a fast-paced, ever-changing environment
Someone who takes initiative, figures things out, and follows through
Ability to stay focused on results, not just activity
Work Monday-Friday 8-5, flexible as needed for client and prospect engagement
Willingness to learn quickly and adapt
What Success Looks Like
Consistently generating new opportunities and building your pipeline
Staying active across multiple outreach channels
Converting conversations into revenue
Maintaining organization and accountability in your CRM
Meeting and exceeding sales goals
What You’ll Love About This Role
Hybrid flexibility (in-office up to 2x/week when not in the field)
Company vehicle provided
Base salary + uncapped commission (1.5% of revenue)
Ability to manage your territory and approach
A fast-moving environment where no two days are the same
You’ll have access to The Middle Six for sales coaching if needed
Requirements
Valid Driver's license
Drug test and background check
Must reside within reasonable driving distance to Alsip and/or Addison IL
The Middle Six is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, genetics, disability, age, veteran status, or any other characteristic protected by law.
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