Why Small Trucking Fleets Are Still Standing [Commentary] – Fleet Management

It’s no secret that the trucking industry is overwhelmingly made up of small fleets. That was true even before the pandemic, but the number grew rapidly when Covid-era spot rates spiked and new carriers flooded into the market. 

Most of those carriers were very small. At the end of 2023, nearly 70% were one- or two-truck operations, according to FMCSA data. Even though they’re technically motor carriers, many of them still think like drivers. In many cases, that works just fine. 

But as they grow, successful small fleets learn to start thinking like a fleet owner and not like an owner-operator.

Somewhere around eight to 15 trucks, the fleet owner can no longer be in every truck, in every conversation, making every decision. Compliance, safety, insurance, and maintenance issues start to stack up. That’s usually when processes start to matter. 

The Hardest Trucking Fleet Size to Be?

For the sake of argument, let’s call a small fleet one that operates between 11 and 100 trucks, which makes up about 7% of U.S. motor carriers.

It might be the hardest size to be. These fleets are too big to manage casually and too small to absorb mistakes. They’re more visible to regulators and insurers, yet they don’t have the resources to copy the playbooks of large carriers. 

And yet, a surprising number of them are still standing after navigating a prolonged freight downturn, rising insurance costs, regulatory shifts, and ongoing technology mandates that have left very little room for error 

Small Size Offers Pros and Cons for Trucking Fleets

Often, small fleets have things going for them that larger fleets don’t, characteristics that may have helped many survive over the last few years of freight recession. 

For instance, many small motor carriers didn’t have the kind of buffer as big fleets in terms of capital or customer contracts. But at the same time, they weren’t as burdened by high fixed expenses for corporate offices and the like, giving them more operational flexibility.

Instead of trying to get bigger, many small carriers got smarter. They cut costs, doubled down on customer relationships, and invested in technology that made sense for their particular operations.

Over the past year, our editorial team has been spending more time with small fleet owners, and in 2026 we’re doubling down to offer practical guidance where big-fleet playbooks don’t fit. 

What’s Working for Small Trucking Fleets 

Last year, we spoke with several small fleet owners who had not only survived multiple freight cycles but grown through them. Some common themes emerged. 

Driver Relationships

They often have lower turnover because they have more of a personal connection with drivers, prioritize treating them well, and can respond faster to driver issues. 

Jamie Hagen, whose Hell Bent Xpress has about 12 trucks, said that sometimes that includes telling a customer “No.”

“That’s a hard lesson to learn,” he admitted. “But if you’re up front with people, ‘I don’t have enough trucks this week. Can we make this run next week?’ It usually works out for the better in the end.”

Attention to Costs

Hagen said he realized that being smart with money was the primary directive for a small business owner. 

For instance, he’s passionate about fuel economy. “I’ve never understood the desire to burn more just for fun. I don’t do donuts in my personal vehicles either.”