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Home ›› Technology ›› Tech Startups ›› They Watched the Family Business Get Rolled Up. Then They Built the Version They Wanted to Work For.

They Watched the Family Business Get Rolled Up. Then They Built the Version They Wanted to Work For.

The Coltrain brothers, having seen their family business Dickinson Fleet Services acquired by Cox Automotive, launched Coltrain Onsite Fleet Care in August 2025. Their mobile units are equipped with Miller Trailblazer 330 Air Pak welders and diagnostics, enabling 95% of routine repairs on-site. The company now operates roughly 70 technicians across 15 states, largely east of the Mississippi plus Texas.

iG
iGEN Editorial
July 31, 2026
They Watched the Family Business Get Rolled Up. Then They Built the Version They Wanted to Work For.

Small carriers often operate with an outdated picture of mobile maintenance, and the gap costs them money. According to a FreightWaves report, the Coltrain brothers – Kyle and Kevin – witnessed their family business Dickinson Fleet Services grow from a small Indianapolis operation to a subsidiary of Cox Automotive, then launched their own venture, Coltrain Onsite Fleet Care in August 2025 with a technology-forward approach.

A Business That Did Not Exist Yet

In 1997, Bob Dickinson started Dickinson Fleet Services out of a small operation in Indianapolis. His grandsons Kyle and Kevin Coltrain grew up around it. Their father, Ted Coltrain, and uncle, Mike Dickinson, ran the company as it scaled. According to FreightWaves, the early product was narrow: mobile maintenance in the early 2000s meant oil changes, preventive maintenance, and minor repairs. Most of the job was explaining to customers what mobile maintenance even was, Kevin Coltrain described on The Long Haul podcast.

Both brothers went to work in the family business after college. Kyle, a wide receiver at the University of Central Florida, went into field sales in Tampa. Kevin managed regional operations across multiple markets.

The Roll-Up They Lived Through

Dickinson Fleet Services took on Ridgemont Equity Partners as majority shareholder. In an acquisition announced January 5, 2021, Cox Automotive bought the company outright, folding it into its Pivet fleet services platform. At that time, Dickinson operated more than 700 mobile repair units and employed roughly 800 technicians. Under Cox, the business grew past 1,500 technicians serving more than 14,000 clients annually and was rebranded as Fleet Services by Cox Automotive. In early 2025, Cox acquired the remaining minority stake held by Mike Dickinson and Ted Coltrain.

Kyle’s account of that arc is measured. He describes going from a small family owned business to a private equity backed company to a subsidiary of a large corporation, and says there was good and bad in all of it. His argument is narrower: when large capital arrives, it comes with quotas. The quota that concerned him most was the technician headcount target, because a manager carrying a mandate to add ten technicians in a month will hire someone off a phone screen who says he can turn a wrench. Kyle put it plainly: "a tech in the field does not have a buddy in the next shop bay to ask for help" and is often working nights, early mornings and weekends.

A tech in the field does not have a buddy in the next shop bay to ask for help.

Kevin added that pushing a technician to finish a four-hour job in two means things get missed.

What a Mobile Unit Can Actually Do in 2026

According to FreightWaves, most small carriers are working from an outdated picture. Coltrain’s units are equipped with the Miller Trailblazer 330 Air Pak, a combination welder, generator, and compressor. That single piece of equipment changes the conversation: welding and trailer body work happen in the yard, which Kyle described as close to unheard of in a mobile environment. The company’s own materials put the figure at 95 percent of routine repairs and maintenance handled on site. That covers engine diagnostics through a direct plug into the truck, after-treatment work including DEF system sensors, and diesel particulate filter work.

Capability Traditional Mobile Maintenance (early 2000s) Coltrain Onsite Fleet Care (2026)
Core services Oil changes, preventive maintenance, minor repairs Engine diagnostics, after-treatment, welding, trailer body work
Key equipment Basic hand tools Miller Trailblazer 330 Air Pak (welder/generator/compressor)
On-site repair rate Limited 95% of routine repairs

Growth and Coverage

The brothers launched Coltrain Onsite Fleet Care in August 2025 with seven states of coverage. Kyle told the podcast the company now runs about 70 mobile technicians across 15 states, largely east of the Mississippi plus Texas.

Implications for Fleet Managers

For CTOs and supply chain technology managers, the Coltrain story underscores how purpose-built technology – from advanced welding equipment to onboard diagnostics – can dramatically increase the scope of mobile maintenance, reducing downtime for small carriers. The emphasis on technician quality over headcount quotas offers a model for maintaining service reliability as fleets adopt more digital and automated tools.


Sources: FreightWaves

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