About us

We've Turned Challenges
Into Logistics Wins

2021

YEAR FOUNDED

Winners Transportation started on the road, not in a boardroom. Our founders drove trucks before they built a company, and that hands-on experience shapes every decision we make today.

48

STATES COVERED

Our OTR operation covers the entire lower 48 states. Dry van, reefer, and flatbed freight moving coast to coast with consistent transit times and real dispatch support.

250+

ACTIVE TRUCKS

A growing fleet of late-model trucks and new trailers, maintained on schedule and assigned to experienced drivers who know their equipment and their routes.

Our Team

Meet the Team Behind Convoy©

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Michael Rodriguez

Founder & CEO

Young woman with shoulder-length brown hair wearing a dark gray sweater and small gold hoop earrings, smiling gently.

Sarah Chen

Director of Supply Chain Strategy

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James Patterson

Lead Transportation Consultant

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Lisa Nguyen

Technology Integration Specialist

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David Thompson

Fleet Optimization Manager

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Maria Garcia

Warehouse Operations Consultant

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Our Story

How Winners Became More Than Just a Name

Our results
98%

Driver Retention

250+

Active Drivers

Learn More
Winners Transportation was built by people who started behind the wheel, not behind a desk. Our leadership team came from the cab of a truck, and that firsthand experience shapes everything we do. We know what good dispatch looks like, what real home time means, and what it takes to keep freight moving across 48 states without cutting corners. What started as a small operation out of Oakbrook Terrace, Illinois has grown into a full-service OTR carrier running dry van, reefer, and flatbed freight with a team that stays because they want to.
FAQ

Got Questions? We’ve Got Answers

Don’t find your answer? Contact us.

01

Who is Winners Transportation?
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Winners Transportation LLC is a privately owned OTR trucking company based in Oakbrook Terrace, Illinois. We haul dry van, refrigerated, and flatbed freight across all 48 contiguous states. Our company was built by people who started as truck drivers and grew the business from the ground up.

02

What makes Winners different from other carriers?
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Our leadership team has real experience behind the wheel. That means we understand driver needs firsthand, we don't overpromise on loads or home time, and we maintain direct communication between drivers and dispatch. We run our own trucks with our own drivers. No brokering, no middlemen.

03

Where is your headquarters?
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Our office is located at 1 Mid America Plaza Ste 300 #7004, Oakbrook Terrace, IL 60181. Our dispatch team operates from here and supports drivers running routes across the entire continental United States.

04

Are you currently hiring?
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Yes. We're actively hiring CDL Class A company drivers and onboarding qualified owner operators. Call recruiting at +1 (331) 336-4909 or visit our Contact page to start the process.

05

How do I get a freight quote?
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Call our HQ line at +1 (708) 571-0464, email info@winnerstrans.com, or fill out the form on our Contact page. We typically respond within one business day.