Outside Sales Representative

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 Full benefits package (Health insurance, 401k, PTO, etc.) 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.

Pay:

$68,000.00 - $150,000.00 per year

Benefits:

Health insurance Paid training Professional development assistance

Work Location:

Hybrid remote in Alsip, IL 60803