Transportation 2025: WEBB ESTES

Estes follows in his great-grandfather’s footsteps leading Estes, North America’s largest privately owned freight carrier. In 2023, he was promoted to president and COO, succeeding his father, Rob Estes, who is now board chairman and CEO.

The 94-year-old Estes Express has more than 24,000 employees. Its fiscal 2024 revenue totaled $5.8 billion.

Estes has acquired 37 terminals from the former transportation provider, Yellow, after the Tennessee-based company’s bankruptcy. In 2024, it added nearly 7,000 trailers and over 700 doors through six new terminals and the relocation of 14 others

to larger facilities. Estes has more than 300 North American terminals and over 10,500 tractors.

In March, Estes Express announced it’s partnering with nonprofit Smart Freight Centre on efforts to reduce its carbon emissions. The company was one of two to win an inaugural Sustainability Pathfinder award from industry outlet Transport Topics in 2024.

A William & Mary alum, Estes joined the company full time in 2007.

WHAT PEOPLE WOULD BE SURPRISED TO LEARN ABOUT ME: I’m a graduate of the Estes Driving School. I still keep my CDL and have a great appreciation for what our professional drivers do each day.

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