With the July 31 deadline fast approaching to enter to compete in Overdrive's 2026 Small Fleet Championship, today we're checking in with with Oberman Logistics owner-operator and 2025 Small Fleet Champ Wes Oberman.
Oberman prides himself on the simplicity and, yes, transparency his fleet offers to owner-operators who lease on with him. It's a straight 15% of a load's gross charged, with a separate, minimal fixed chargeback otherwise for ELD service and permits, and clarity on self- and/or managed-dispatch choices.
It's proved a refreshing alternative to the clouded transparency owners have dealt with for so many years in so many different quarters, not just lease arrangements.
Results for Oberman? Growth, simply put. Since Oberman Logistics walked away with the 2025 Overdrive's Small Fleet Champ award in the 3-10-trucks division, the company's brought on several leased owners to a current 14 total trucks in the operation.
That includes his own 2026 Kenworth T680. Not that he's been in that unit running the roads much lately, right at the size that, often enough, small fleet owners find back-office pressures rise to levels unmanageable from the cab.
He and his wife and business partner, Laura, actually hired a former owner-operator who'd retired from Oberman after several years of hauling leased there, to dispatch. But Oberman's been building infrastructure, too -- he's been busy coding, that is.
You heard that right. Coding. With the help of Claude Code and ChatGPT, he's built an Oberman Logistics native TMS hub that will cost him just $55/month ongoing rather than $2K-plus he was quoted for commercial systems, all of them with more functionality than he'd ever use.
Wes Oberman from the stage addressing NASTC conference attendees after accepting the 2025 Small Fleet Champ award and title belt. Enter for 2026 before the July 31 deadline via this link.
His custom-built system runs right from a subdomain on his company website to handle loads after booking:
- Upload the rate confirmation to the system, and an extractor reads and fills in TMS fields to start dispatching the loads. Crucial here is it adds notes for the driver prominently -- Oberman gave the example of a $100 fine for late pickup, too often unnoticed.
- After a close check of the load entry and owner-operator assignment, the TMS emails the driver with load details.
- At load completion, the back office uploads the proof of delivery or a copy of the bill of lading -- the TMS is set up to email to broker customers, and Oberman accounting is CC'd on the email for a paper trail in case it's ever questioned.
- Finally, the load moves to the accounting function of the TMS, where with a single click the Obermans can output an invoice, combining it with the rate con and POD/BOL in a single pdf document.
- Tracking after the invoice is sent counts days since issuance, easy to see at a glance in the list of outstanding debts, "so we know who to call" for past-due payment, Oberman said.
[Related: Brokers' contract nickel-and-diming incentivizing speed, fatigue?]
The 2025 Small Fleet Champ built the system after a talk with a non-trucking friend about just what was possible today using Claude Code.
He'd used ChatGPT semi-regularly for research and his own numbers analysis, so started there by telling that engine what he wanted the TMS to do, then asking it for Claude Code prompts he'd input in the coding module.
After a lot of back-and-forth between the two engines, he utilized Supabase and Github to build out the structure of the application, and Vercel to host it, accessed by end users within his ObermanLogistics.com domain. The Resend company's service is set up to handle email notifications to leased owner-operators, broker customers and the back office.
He envisions improvements, too, with expanded functionality.
"I eventually want to make it so that the owner-operators can upload their own BOLs" and/or PODs to the system, he said, possibly integrated with Oberman Logistics' Samsara ELDs to "geofence when they're within five miles" of a delivery to auto-email the broker. "Our biggest time eater is answering brokers’ emails" checking in on load status in-trip.
As noted, he's padding the bottom line and poised for further growth simply by not spending the money on a commercial TMS. Yet it all required a significant time investment up front: 5-6 hours, 7 days a week, for a full three weeks and some change, he estimated, to get functionality rolling before testing the system for bugs.
He's benefiting on the other side, though, with an estimated 20 hours' worth of work saved weekly with the system up and running.
He "also made a settlement/payroll program that automatically calculates everything, so no chance of underpaying our guys," he said, speeding up their payments, too, in the process.
Enter to compete for one of two Overdrive's 2026 Small Fleet Champ title belts at this link before the deadline July 31.
"I'll be there, for sure," Oberman said of the annual conference of the National Association of Small Trucking Companies, set for October 29-31 this year in Nashville, Tennessee. We'll host four finalist small fleets there in the final round for the title belt, recognizing the achievements alongside hundreds of NASTC members and other trucking peers.
Enter by July 31 to compete in the 2026 Small Fleet Championship.
Oberman's been a member for years now, he noted, with good results from NASTC's insurance services agent this year at renewal, even with growth, a story told in this May edition of Overdrive Radio.
"It wasn’t that hard" other than all the time put in at the computer screen, noted Oberman of the TMS buildout. "Just a lot of reading, really."
The 2025 Small Fleet Champ is in talks with two additional owners to get Oberman Logistics to 16 total power units before the year's out, and hopes to hit 20 by May 2027 if the plan holds.
Original story about Wes Oberman published September 23, 2025, follows below:
Oberman Logistics, headquartered in Huntingdon, Tennessee, got its start officially in October of 2019 with its eponymous owner-operator Wes Oberman and just his single truck OTR. Yet from the get-go he had a plan in place to expand, to build a small fleet with a stake in the success of other owner-operators.
"I felt there was a gap in the industry for good, honest companies that wouldn’t gouge you" as an owner leased on with fees in excess of what's really necessary, he said. The conviction came after some years researching the lease contracting programs of other, well-known carriers, all with variations on percentage contracts.
"I hopped in the truck, and I ran myself for a year and a half or two years" with authority, he said, to get a clear sense for his own costs and revenue opportunities. He then developed a standard contract he started advertising via the Oberman Logistics website. The company's charge to owners leasing to Oberman to self-dispatch or be dispatched by Oberman and his wife, Laura, also working full-time in the business, is 15% of any load's gross, and a maximum $135 a week. That $135 includes insurance -- at a max $7,020 annually for insurance alone, it would be considered a very fair rate in today's market for an independent with authority. Oberman-leased owner-operator Gary Wentzel put it this way: "They're losing money on our insurance" given the inexpensive nature of the chargebacks, in his view.
On top of insurance, the weekly charge also covers ELD expenses, decals, various permits, IFTA administration covered by the company and access to the Oberman's fuel card through the National Association of Small Trucking Companies' decades-proven discount fuel network. (Oberman's insurance is set up through NASTC's insurance program as well.)
Operators running oversize freight will pay for those permits. Standard operating expenses like tolls and fuel, of course, are also leased owners' responsibility.
Oberman set out to keep administrative fees simple, ultimately, and as transparent as possible in hopes of building a home for a bevy of owners. "A lot of carriers charge $250 a week" to an owner-operator, easy, above and beyond whatever percentage of the gross they take, Oberman said. In his view, "these companies are taking too much money. I don’t think that 15% we take should be pure profit."
There's some evidence the commitment to cost sharing is working. As owner and manager of a small fleet that as of early August was now up to 11 total owner-operators, including Wes himself (up from nine at the end of 2024), Oberman wants to demonstrate to any owner he works with that he's truly invested in what they do. Not as a profit center for his business, but as real support for the long haul. Oberman Logistics' clear success delivering those goods makes the business a semi-finalist for Overdrive's 2025 Small Fleet Champ honor.
[Related: Derrick Wolfe has built a 'sweet' tanker business in New York's Finger Lakes region]
Skin in the leased owner's game
Owner-operator Gary Wentzel is based in Wernersville, Pennsylvania, and has been leased to Oberman Logistics for about three years. Wentzel sees clearly Wes Oberman's approach to the business. "He could make a lot more money," Wentzel said, "but he wants good guys who will do the job well. [The Obermans] aren't going to be millionnaires anytime soon."
Wentzel owns a low-pro step deck. Oberman Logistics he dubs "the only place I've been I've never had a complaint," he said, and lauds a simple and easy sign-on process and fair and honest dealings. "I’ve been there almost three years. I’ve never had a complaint. The best thing I can say about these two, Wes and his wife: they're the most honest people in this trucking racket I’ve ever met."
The simplicity of the 15% take, the fixed weekly deduction. "What they tell you are your costs outside the 15%" are in fact the costs, Wentzel said. "They pay our IFTA whether we owe or don’t owe," too, in his case. "They take care of all that." Gone are the days of getting surprised by a "$600 bill at the end of the quarter," he added.
[Related: Fuel taxes: Finding the cheapest fuel about much more than pump price]
Oberman Logistics would go on to win the 2025 award in the 3-10-trucks division (Access profiles of all past semi-finalists via this link.) Four finalists for the 2026 champ award will travel to Nashville in October. Enter here to compete before the July 31 entry deadline.
He takes the rate, or declines, and that's that.
The 10 owners leased to Oberman are headquartered across the country and all running exclusively for Wes and Laura and company. "We've got one guy in New York, in West Virginia and Montana," Wes Oberman said. A couple in Wyoming. Colorado, Kentucky, Michigan. Ohio. "It took just about three weeks of us advertising" before the first owner made the jump to the company, Oberman said, a former Landstar-leased owner with a dry van who was accustomed to self-dispatch.
Wes and Laura Oberman
The long square nose, though: "The fuel was crazy," he said, lucky to "get 5.5 to 6 mpg."
The 389 was a looker, though, that's certain, shown here loaded.
In early 2025 he purchased the 2026 Kenworth T680 shown up top for himself, likewise with a Cummins in it. "10 miles to the gallon," no kidding, he said. "I don't idle, and don't typically stay the night out. I'm fairly local," between his home base and Memphis to the West and Nashville to the East. "Home every night."
Oberman's operators are about 50/50 on self- and full-service dispatch, he said, though as Wentzel's case shows there are gradations in some cases. Oberman himself likes the help. Laura Oberman stays plenty busy, that's sure -- every load ultimately comes through her, likewise payroll and settlements, "all that stuff," Wes said.
[Related: Small fleet, big benefits with move toward improved stability]
Road to burgeoning success, growth
Wes Oberman has been trucking in some form or another since he got his CDL at age 19, some 22 years ago in California, where he's from originally. "I filled in for log-truck drivers when they got sick," he said, to start. He was a logger himself, and the owner of the oufit he worked for "paid for me to get the CDL."
His father got sick and he moved be to be closer to him in Northern California, then, and worked for Sysco, supplying food service operations. "Hard work," he said, "but it pays really well."
He knew through it all that he'd only go so far "driving for someone else. You can't really get past the ceiling of it," he said. Looking around, too, his colleagues showed the wear and tear of the work they were doing.
"So many people blew their knees out" routinely, he could see. "I knew I’d eventually have to leave there, somehow -- my body wouldn’t live up to" the long-term challenge. Oberman's 41 today.
He and Laura bought their house in California in 2008, right at the bottom of the housing market during the crash of that year. "Food service never stops," he said, one great thing about the work for Sysco. "It's recession-proof," to an extent.
The National Association of Small Trucking Companies sponsors the Small Fleet Championship. Finalists receive a year's worth of membership in the association, with access to a myriad of benefits from NASTC's well-known fuel program to drug and alcohol testing services and much more. All will be recognized at the association's annual conference, where the winners will be announced in late October in Nashville, Tennessee. Find more about the association via their website.
Ultimately, the Obermans settled on Tennessee and, when they sold their California home in 2019, they bought the Pete and flatbed trailer and ended up with extra cash left over. Oberman Logistics thus "started with no debt," which would be key during the early-2020 COVID storm and the collapse of freight markets.
It was a brief downturn, though, and Wes had been getting familiar fast with brokers for flat freight in the region around Huntingdon. Given he knew what he wanted to do in terms of building that home for other leased owners, wherever they happened to be, he's kept to that brokered-freight model. "I didn't see the point in pursuing direct customers," he said. "If I had direct customers, I'd have to manage" the schedules of owners directly, contrary to the no-forced-dispatch model he was adopting for his contracted owners.
He himself started out running "straight off the load board," he said. Today, though, relationship-building has progressed well. "We have brokers we can call when we're in certain areas."
Among those is Ryan Transportation Senior Carrier Sales Representative Ian Mowery, who noted Ryan's "worked with Wes Oberman and his team for quite some time, and they’ve consistently proven to be a reliable and professional partner" with "consistency, attention to detail, and a strong commitment to service."
Mowery lauded company culture at Oberman as placing real value on "communication, accountability and problem-solving -- all traits that are critical" in trucking.
[Related: First load free? Owner-operators share slick salesmanship tricks, broker icebreakers, more]
Oberman Logistics "runs a tight ship," in short, he added. "They embody the kind of excellence that keeps this industry moving."
Wes has pivoted when necessary, too, to combat freight situations -- "whether it's a shipper dying or mega-carriers running down the rate," he said.
Out of Memphis, for instance, for years he "ran Owens Corning shingles," he said. "It paid amazing, and you were in and out very quickly."
Over the last year, big fleets bid down the rates out of the facility, though, and now a lot of Wes's own Memphis loads through a different broker are "steel plate running to Jasper, Alabama," he said. "You have to be able to pivot."
Laura helps in that regard for some among owners leased there. Any owner leased to Oberman will "get a login with DAT, and from there they can see all the loads and negotiate with brokers" as much or as little as they like, Wes said. "Sometimes brokers will call and verify any owner works with us, and I appreciate that. They'll send the rate-con to what they have on file for the Oberman Logistics account," and it's shared with the owner-op set to haul the load.
"Laura bargains and gets me a little more money than" brokers offer most of the time, said owner-operator Wentzel. He'd had his 8-mpg 2016 Freightliner (automatic transmission) leased to Daily Express prior to joining up with Oberman. He was pulling often-oversize freight with Daily trailers at the time when he "bought the low-pro step deck, and they wouldn’t pay me any more percentage," he said. He decided to leave and simply "got on Google and was looking for smaller companies in the Midwest."
Gary Wentzel with that Freightliner and one among many loads he's hauled for Oberman.
Still running permitted overlength or otherwise oversize freight at times, Wentzel notes another assist from the back office at Oberman, too, with permits "on-time every time -- there's an outside place that arranges them for me, and I get them right away," he said.
Fuel discounts were running in the 50-70-cents/gallon range off the pump price in early August, he added.
Another of owner-operator Wentzel's loads for Oberman was this vintage fire truck, not the only one moved for a buyer who restores 1960s-'80s vintage trucks for parades, said Wes. Delivery point: The buyer's house.
Owner-operators run their own dashcams, said Oberman, yet video wasn't necessary to clear just a single crash on the Oberman Logistics record to date. Coming up on a construction site and slowing, the Oberman operator involved took two hits in the rear. "One driver was on their phone," said Wes, "the one that was injured."
Fault was right there on the police report in this case, with Oberman's operator deemed "not at fault," said Wes Oberman. Getting the crash deemed nonpreventable through the Federal Motor Carrier Safety Administration's crash-review program "took three-four weeks," and generally "wasn't that hard."
[Related: Preventable or not? When to use DataQs to request crash reviews for preventability]
The most time-consuming part was getting the copy of the police jurisdiction's crash report. "We had to track that down and pay to get it sent to us," said Oberman, after a month or so. It's a feather in the owner's cap. Wes Oberman's most proud of the safety record he and his owner-operators have been able to maintain this far into their history as a fleet.
"We get compliments on it almost every day" dealing with brokers, Wes said of that record, a boon in what's been a tough few years for brokered freight. Oberman Logistics, through it all, is excelling above and beyond the competition. "We are a truly mom and pop company. Just me and my wife, no employees otherwise."
Justifiably, Wes notes he's "pretty proud" of the growth thus far, he said, and looking forward to the business's future.
[Related: 2026 Small Fleet Championship: Last month to enter!]
