100 Years of Covering Trucking: Celebrating Long-Lived Fleets
Estes Names Webb Estes President, COO
Webb Estes represents the fourth generation of the Estes family to lead the company, which was founded in 1931.

Webb Estes, who most recently served as vice president of process improvement, was promoted to president and chief operating officer.
Photo: Estes Express Lines
Estes Express Lines promoted of Webb Estes to president and chief operating officer. Webb Estes is the fourth generation of the Estes family to lead the company, which was founded in 1931.
Former Vice President and COO Billy Hupp has transitioned to the role of VP of the board and corporate executive VP. Rob Estes, formerly the company’s president and CEO, will continue his duties as chairman of the board and CEO.
Webb Estes most recently served as VP of process improvement. In addition to his previous role, where he oversaw much of the company’s day-to-day operations and spearheaded several technological improvements, Webb has hands-on expertise of Estes’ operations through managing a terminal, driving company trucks and moving freight on the dock. He also holds a commercial driver’s license.
Estes Express Lines was named one of HDT's 2021 Top Green Fleets.
More Fleet Management

For Nicky Cupp, Fleet Innovation Starts With Frustration
HDT Truck Fleet Innovator Nicky Cupp turns everyday pain points at Fraley & Schilling into opportunities for better technology and smarter processes.
Read More →
Adam Buttgenbach’s Approach to Electric Trucks: Start With Where They Fit
HDT Truck Fleet Innovator Adam Buttgenbach helped PepsiCo build one of North America’s largest EV fleets by focusing on where electric trucks make operational sense.
Read More →
Deen Albert: Let Automation Do the Math, People Make the Decisions
HDT Truck Fleet Innovator Deen Albert makes sure people are still at the heart of operations at Grand Island Express, even while adopting artificial intelligence tools. AI-assisted dispatch helped boost revenue 25% with the same number of trucks.
Read More →Trimble’s New AI Agent Takes Aim at Fleet Back-Office Busywork
Arc Agent works across Trimble TMS products to automate repetitive tasks such as freight orders, maintenance, invoices, fuel costs and more.
Read More →
How HDT’s 2026 Truck Fleet Innovators Are Rethinking Fleet Operations
Meet five trucking leaders who are challenging assumptions, solving operational problems, and putting innovative ideas to work.
Read More →
Tight Trucking Capacity Pushes Rates Higher Even as Freight Volumes Fall
“Spot rates moving ahead of contract rates have historically signaled a tightening market, but we haven’t seen a capacity-driven market quite like this one,” said DAT's Dean Croke.
Read More →
Import Cargo’s Early Peak Season is Winding Down
There was an early start to peak season this year at the nation's gateway ports, as retailers brought in merchandise ahead of tariff changes in late July and responded to other supply chain uncertainties,
Read More →
Fewer Cargo Thefts, Bigger Losses: Criminals Target Higher-Value Loads
CargoNet says organized theft rings are stealing fewer shipments but choosing more valuable freight, including metals and technology, resulting in record losses.
Read More →
How Innovative Trucking Leaders Turn Change Into an Advantage
As the pace of change accelerates in trucking, the fleets that adapt best have more than the latest technology. They have cultures that embrace improvement.
Read More →
Freight Broker Bonds Just Got Harder to Get. Here's What That Means for Your Fleet.
When it gets harder for a freight broker to prove they are financially sound, the ones who cannot clear that bar get pushed out of the market. And those are exactly the brokers who used to leave motor carriers holding the bag.
Read More →
