Owner-operator and Overdrive 2025 Small Fleet Champ Wes Oberman's mostly-open-deck Oberman Logistics business makes good on growth goals with a transparent promise to owner-operators leasing there: 15% of the gross for costs, no insurance chargebacks.
Since his big win last fall in the 3-10-trucks division, the owner-operator's moved to 13 trucks, including his own 2026 Kenworth T680, by keeping that promise.
At insurance renewal early this year, even with growth in the fleet, he reduced his overall insurance outlay in an age where liability costs for motor carriers of all stripes just continue to roll up and up and up.
How he did it: Acting on lessons learned from his National Association of Small Trucking Companies insurance agent about engagement with data the business's operations generate. I wrote about his experience managing ELD data last Fall before the renewal, and in this week's edition of the Overdrive Radio podcast he details the result:
"We had companies fighting over our business this year. It was a nice turn."
His big win as Small Fleet Champ contributed, in ways small and much larger, where it matters.
"I have added that we are the Small Fleet Champs at the bottom of my email signature," he said, thus routinely flagging the recognition in any communication with a potential insurer.
More importantly, the award was a "talking point when talking to all these insurance companies" in renewal negotiations, he added.
Enter your own business in the 2026 Small Fleet Championship at this link.
But he knows it's the real engagement with safety data that he and his leased owners show, in addition to proven safety performance OTR, that's likely most moving the needle.
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Now not only can his insurance provider see and share those with him, whereupon he'd make the call on how to talk to any leased owner about it, if at all. Leased owner-ops can see it themselves in his current setup.
"Any type of safety event, it can send it directly to the owner-operator," he said of his current system. "Nobody's perfect," he added, no need to "hound these guys." All leased owners "can see what the insurance companies see" now, as can Oberman.
Parties actively engaged means more insurer comfort with his fleet's risk, and that means lower costs and preservation of the transparency in his 15% pricing for owners leased long-term.
"That's my main pitch to owner-operators," that "our deductions are so low" for a reason, he said. "If our insurance rates get jacked up, we will have to raise our deductions," hitting the entire group of owners.
Every Oberman Logistics-leased owner-operator well knows the tradeoff they're making here -- consent to being monitored (for lack of a better word) in these ways for the benefit of cost reductions, better profits, stability in the operation.
[Related: ELD-data engagement: Your insurance premiums could depend on it]
Enter the 2026 championship at this link. Fleets 3-30 trucks are eligible to compete for a chance at the title belt, a trip to Nashville in October, and other perks.
He plans to add three more owners this year to a max of 16 trucks, continuing slow growth to avoid big insurance downsides, and potential new staff in the office to help Laura's growing work burden.
He’s got a bit of leg up being mostly flatbed in the current moment, in spite of difficulties keeping fuel costs in check since the beginning of the war in Iran. Brokered flatbed freight’s really been on a rates tear since last Fall, into the present, too, he noted.
He’s doing everything he can to set up for continued success, clearly, and if that describes your multi-truck operation, get your fleet in the Small Fleet Champ running at this link. More detail on Oberman's approach in this week's podcast:
