Trailer Sales Representative

Midway Trailer Sales & Service, Inc; Ottawa (IL); On-site; USD 40,000 - 60,000; Full time

Benefits offered by this job

Competitive pay plus commission

Health, dental, and vision insurance

Paid vacation and holidays

Simple IRA with company match

Job summary

Midway Trailer Sales & Service, Inc in Ottawa, Illinois is looking for a motivated Trailer Sales Representative. In this role, you'll manage the entire sales process and create lasting customer relationships. Strong communication skills, a self-starter mindset, and sales experience are essential. The position offers competitive pay (salary plus commission), health benefits, and a full-time schedule with daily customer interactions. Join us and make an impact with your sales expertise!

Qualifications

• Ability to thrive independently and as part of a team.
• Positive attitude and ability to turn conversations into sales.
• Track record or strong drive to generate sales.
• Pride in customer service.

Responsibilities

• Manage the entire sales journey from conversation to delivery.
• Connect with customers and recommend trailer solutions.
• Close deals while ensuring agreements meet requirements.
• Handle licensing, paperwork, and payment processing.
• Build relationships for repeat business.

Skills

Strong communication and negotiation skills

Sales experience

Organizational skills

Self-starter mindset

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