Trailer Sales Executive: Own the Full Sales Journey

Midway Trailer Sales & Service, Inc; Litchfield (IL); On-site; Full time

Job description

Benefits:

• Simple IRA Match
• Simple IRA
• Dental insurance
• Health insurance
• Paid time off
• Vision insurance

Trailer Sales Representative

If you love talking to people, closing deals, and being in control of how much you earn—this is your kind of role.

We’re looking for a motivated go-getter who’s ready to own the sales process from start to finish. This isn’t just about selling trailers—it’s about building relationships, solving problems, and creating customers who come back again and again.

What You’ll Bring

• A self-starter mindset with the ability to thrive both independently and as part of a team
  
  
• A positive, friendly attitude and a natural ability to turn conversations into sales
  
  
• Strong communication and negotiation skills—you know how to connect, listen, and close
  
  
• A track record (or strong drive) to consistently generate sales while earning customer trust
  
  
• Strong organizational skills and attention to detail
  
  
• Pride in doing right by the customer—not just making the sale
  
  
• Sales experience preferred (trailers or related industries a plus)
  
  

What You’ll Do

As a Trailer Sales Representative, you’ll manage the entire sales journey—from the first conversation to final delivery and beyond.

• Connect with customers, understand their needs, and recommend the right trailer solutions
  
  
• Prepare accurate quotes and guide customers through pricing, financing, and trade-in options
  
  
• Close deals confidently while ensuring all agreements meet company and state requirements
  
  
• Handle licensing, paperwork, and payment processing
  
  
• Build and maintain strong relationships to drive repeat business and referrals
  
  
• Partner with the shop team to ensure repairs, inspections, and deliveries exceed expectations
  
  
• Stay on top of inventory—monitor stock, place orders, and keep records accurate
  
  
• Perform weekly lot checks to maintain presentation and condition
  
  
• Maintain accurate records in Lightspeed and other systems
  
  
• Develop expert knowledge of trailer models, features, and warranties
  
  
• Support marketing efforts both online and on the lot
  
  
• Provide top-notch after-sales support to keep customers coming back
  
  
• Grow relationships with fleet accounts, dealerships, and industry partners
  
  
• Represent the company at trade shows and networking events when needed
  
  

What You’ll Get

• Competitive pay: salary plus commission—your success directly impacts your earnings
  
  
• Health, dental, and vision insurance
  
  
• Paid vacation and holidays
  
  
• Simple IRA with company match
  
  

Work Details

• Full-time
  
  
• Monday–Friday day shift + Saturdays 8am–2pm (with a weekday off)
  
  
• Mix of office work and being out on the lot
  
  
• Daily interaction with customers, vendors, and the service team