Updated September 2026
Best Owner-Operator Companies in Sheboygan, Wisconsin (September 2026)
Lanefinder tracks 593 owner-operator carriers hiring in Sheboygan, Wisconsin. Rankings below reflect September 2026 data: pay percentiles, FMCSA safety, benefit prevalence, and operational performance. RAY'S TRANSPORT INC leads with an average gross weekly revenue of $8,500 and an average $2,000 sign-on bonus. WINNERS TRANSPORTATION LLC follows at $2,657/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 September 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 | $6,684 | $5,277 | +27% |
| Riders-allowed policies | 90% | 80% | +10 pt |
Source: Lanefinder index, September 2026
Among the figures above, average weekly pay is where Sheboygan, Wisconsin differs most from Wisconsin — 27% above statewide.
Sheboygan, Wisconsin's top owner-operator carriers right now
The top of the list is RAY'S TRANSPORT INC at $8,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1RAY'S TRANSPORT INC — $8,500/wk
RAY'S TRANSPORT INC tops the Sheboygan, Wisconsin ranking with the strongest composite score across pay, safety, benefits, and operational signals. RAY'S TRANSPORT INC sits in the 94th percentile for gross weekly revenue among Sheboygan, Wisconsin carriers. RAY'S TRANSPORT INC's FMCSA score is strongest on driver fitness — 87th percentile. Lanefinder's application data flags RAY'S TRANSPORT INC as a responsive employer.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC's top FMCSA dimension is driver fitness, in the 92nd percentile. Application-response data flags this carrier as a responsive employer.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC's top FMCSA dimension is hours-of-service compliance, in the 96th percentile. LOAD MONSTER INC tracks as a responsive employer on application-response data.
Also in the top 10: #4 WESTERN MOUNTAIN TRANSPORT INC at $8,750/wk, #5 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #6 SWEET EXPRESS LLC at $8,500/wk, #7 WIDER GROUP INC at $6,250/wk, #8 BLUE LIGHTNING LOGISTICS at $7,000/wk, #9 Ali Star Inc at $10,000/wk, #10 KILO METER LOGISTIC 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, 74% 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 September 2026.