Updated July 2026
Best Owner-Operator Companies in Sheboygan, Wisconsin (July 2026)
Lanefinder tracks 590 owner-operator carriers hiring in Sheboygan, 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.
Sheboygan, Wisconsin vs Wisconsin: the numbers that diverge
| Sheboygan, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,599 | $5,295 | +25% |
| Riders-allowed policies | 88% | 78% | +10 pt |
Source: Lanefinder index, July 2026
Among the figures above, average weekly pay is where Sheboygan, Wisconsin differs most from Wisconsin — 25% above statewide.
Sheboygan, 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 leads the Sheboygan, Wisconsin market on combined gross revenue and ranking score this month. ROLLING ON WHEELS LLC ranks in the 96th percentile for driver fitness on FMCSA SAFER data. The carrier tracks as a responsive employer on Lanefinder's data.
#2WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC's top FMCSA dimension is hours-of-service compliance, in the 96th percentile. Application-response data flags this carrier as a responsive employer.
#3INLAND EMPIRE LLC — $7,875/wk
INLAND EMPIRE LLC pays above the 84th percentile on gross weekly revenue for the Sheboygan, Wisconsin market.
Also in the top 10: #4 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #5 SWEET EXPRESS LLC at $8,500/wk, #6 OVERLOG INC at $3,613/wk, #7 WIDER GROUP INC at $6,250/wk, #8 BLUE LIGHTNING LOGISTICS at $7,000/wk, #9 BB8 FREIGHT CO at $12,666/wk, #10 C & G TRANSPORTATION INC at $7,500/wk.
What Sheboygan, Wisconsin drivers actually run
8% of Sheboygan, Wisconsin's active CDL postings are regional and 92% are OTR; local plus semi-local accounts for the rest (0%).
Across Sheboygan, Wisconsin CDL postings: 2% with guaranteed pay, 27% dedicated, 93% take-truck-home, 75% pet-friendly, 71% 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 Sheboygan, Wisconsin
- CDL driver salary in Sheboygan, Wisconsin
- Best owner-operator companies in Wisconsin
Where this data comes from
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.