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Customer Sales Representative

Chicago, IL

Why OTR?

OTR Transportation sets itself apart as more than just a logistics company; we're a dedicated team committed to providing customized over-the-road shipping solutions, with a special focus on temperature-controlled and time sensitive freight. Our expertise allows clients to concentrate on their core business, while we ensure their shipping needs are met with precision.

Our strength lies in our skilled professionals, who bring innovation and excellence to every aspect of our services. This dedication makes us a trusted partner in the logistics industry, adept at meeting the unique challenges of temperature-controlled transportation. We help our clients achieve their objectives by delivering flexible, reliable, and specialized shipping solutions.

The Role:

We’re looking for a Client Sales Executive to join our dynamic team. In this role, you'll be responsible for prospecting and developing new business, nurturing relationships, and managing a growing book of freight customers across the U.S. and Canada. This is a high-impact role for someone who thrives in a fast-paced environment and loves the challenge of building strong, lasting client partnerships.

What You’ll do:

  • Build and manage long-term customer relationships through outbound prospecting and daily client engagement.
  • Drive truckload freight sales with a focus on trustreliability, and service excellence.
  • Collaborate across departments to ensure seamless service and strong customer experiences.
  • Meet and exceed KPIs including outbound calls, on-time delivery performance, and proactive tracking.
  • Use OTR’s tech tools and analytics to make smart, data-driven decisions.
  • Grow your book of business using a multi-channel approach: phone, email, LinkedIn, and more.
  • Execute a structured sales process — while bringing your own entrepreneurial style.

Experience/Qualifications:

  • 3+ years in a customer sales role for a freight brokerage.
  • Ability to thrive under deadlines, drive results, multi-task, and work with a sense of urgency.
  • Demonstrated skills in building relationships and establishing rapport with colleagues, leaders, and clients.
  • Capable of working independently as well as collaboratively across the company
  • Driven, enthusiastic, resilient, agile and highly motivated.

Benefits at OTR:

  • Competitive, uncapped, commission structure
  • Complete benefits package including Medical, Dental, Vision and Paid Time Off
  • 401(k) with matching
  • Office happy hours
  • Free lunch on Fridays
  • Wellness benefits
  • Parking available for a convenient and secure daily commute
  • Being a part of an exciting, growing team

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