Semi-Trailer Sales Representative

Remote in Wisconsin | Base Salary + Uncapped Commission

Ready to take ownership of a growing sales territory with the autonomy to build your business and the support of an established team behind you?

We’re seeking an experienced Semi-Trailer Sales Representative to develop new business and grow existing customer relationships throughout Wisconsin. Candidates must currently live in Wisconsin or the Chicago metropolitan area and have direct sales experience with both dry van and refrigerated (reefer) trailers.

This is a territory-focused sales role for someone who understands the trucking and transportation industry, enjoys hunting for new business, and knows how to turn customer needs into long-term fleet relationships. You’ll manage the full sales cycle from prospecting and account development through equipment specifications, quoting, negotiation, and delivery coordination.

Semi-Trailer Sales Representative Benefits & Compensation:

• Base salary plus uncapped commission
• Tiered commission structure with increased earning potential as gross margin grows
• Additional commission opportunity on rental and lease revenue
• Medical insurance with PPO and HSA plan options
• 401(k) with up to 4% company match
• Employee wellness programs
• Factory and trade show travel opportunities

Semi-Trailer Sales Representative Requirements & Qualifications:

• Must currently reside in Wisconsin or the Chicago metropolitan area
• Must have direct semi-trailer sales experience with BOTH dry van and refrigerated (reefer) trailers
• 2+ years of successful outside B2B sales experience
• Proven ability to prospect, generate new business, and grow an assigned sales territory
• Experience developing relationships with trucking companies, fleets, transportation companies, or logistics customers
• Strong understanding of trailer specifications and the ability to recommend equipment based on customer needs
• Ability to prepare competitive quotes, negotiate pricing, and close profitable sales
• Independently manage a territory, sales pipeline, customer follow-up, and account development
• Coordinate trailer specifications, inventory, financing, contracts, and deliveries with internal teams
• Must pass a background check and drug screen

Must Haves:

• Sales experience with both dry van and reefer trailers
• Current residence in Wisconsin or the Chicago metro area
• Ability to actively prospect and develop new fleet and transportation accounts
• Experience identifying customer equipment needs and recommending appropriate trailer specifications
• Ability to manage deals from initial prospecting through quote, negotiation, order, and delivery

Semi-Trailer Sales Representative Preferred Background & Skills:

• Experience selling both new and used semi-trailers
• Trailer rental and leasing experience
• Existing relationships within Wisconsin and/or the Chicago-area trucking, fleet, transportation, or logistics market
• Class 8 truck or other commercial transportation equipment sales experience
• Familiarity with dealership operations, title processing, financing, and equipment documentation
• Salesforce or similar CRM experience
• Experience prospecting through LinkedIn, social media, and digital sales platforms
• Strong territory planning, pipeline management, negotiation, and closing skills