Updated July 2026
Best Owner-Operator Companies in Wisconsin (July 2026)
Lanefinder tracks 719 owner-operator carriers hiring in Wisconsin. Rankings below reflect July 2026 data: pay percentiles, FMCSA safety, benefit prevalence, and operational performance. ROLLING ON WHEELS LLC leads with an average gross weekly revenue of $5,500. WINNERS TRANSPORTATION LLC follows at $2,437/week gross. Wisconsin freight moves on I-90 / I-94 through Milwaukee and Madison, with dairy and food processing as the dominant outbound commodity and paper and packaging manufacturing in the Fox River Valley generating consistent industrial loads.
What changed in July 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Wisconsin's top owner-operator carriers right now
The top of the list is ROLLING ON WHEELS LLC at $5,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1ROLLING ON WHEELS LLC — $5,500/wk
ROLLING ON WHEELS LLC is number-one in Wisconsin this month on the composite ranking. Top FMCSA dimension here is driver fitness, in the 96th percentile. Application-response data flags this carrier as a responsive employer.
#2WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC's FMCSA score is strongest on hours-of-service compliance — 96th percentile. WINNERS TRANSPORTATION LLC tracks as a responsive employer on application-response data.
#3SWEET EXPRESS LLC — $8,500/wk
SWEET EXPRESS LLC's gross weekly revenue ranks in the 96th percentile across Wisconsin. Top FMCSA dimension here is controlled-substances compliance, in the 99th percentile.
SWEET EXPRESS LLC leads Wisconsin's top 10 on sign-on bonus, advertising $6,000 for new drivers.
Also in the top 10: #4 WIDER GROUP INC at $6,250/wk, #5 OVERLOG INC at $3,145/wk, #6 BLUE LIGHTNING LOGISTICS at $7,000/wk, #7 POPE TRANSPORT INC at $7,000/wk, #8 BB8 FREIGHT CO at $12,666/wk, #9 TP TRUCKING at $8,500/wk, #10 JK MOVING & STORAGE INC at $4,975/wk.
How drivers spend their time on the road in Wisconsin
Of active CDL postings in Wisconsin this month, 12% are regional and 85% are OTR (long-haul). Local and semi-local routes account for the remaining 3%.
Across Wisconsin CDL postings: 2% with guaranteed pay, 28% dedicated, 91% take-truck-home, 72% pet-friendly, 68% riders-allowed.
Driving CDL in Wisconsin
Wisconsin freight moves on I-90 / I-94 through Milwaukee and Madison. Dairy and food processing are dominant outbound commodities — Wisconsin's reefer freight is a national-scale segment. Paper and packaging manufacturing in the Fox River Valley generates consistent industrial loads. Great Lakes ports at Green Bay and Superior handle bulk cargo. Cost of living is moderate. Wisconsin has a high graduated state income tax. Winter is severe — lake-effect snow off Lake Michigan affects the eastern third of the state; ice and salt corrosion eat equipment faster than southern states.
Related guides
- Best trucking companies in Wisconsin
- CDL driver salary in Wisconsin
- Best owner-operator companies in the United States
The methodology behind the rankings
Compensation, FMCSA safety, benefits, and operational performance — weighted 30, 25, 25, and 20 percent respectively. Compensation extends beyond headline pay to include sign-on bonus tier and settlement cadence. Benefits scoring differs by hiring type because the perks that matter to a W2 driver and a contractor are not the same. Updated July 2026.