Updated May 2026
Best Owner-Operator Companies in Sheboygan, Wisconsin (May 2026)
Lanefinder tracks 595 owner-operator carriers hiring in Sheboygan, Wisconsin. Rankings below reflect May 2026 data: pay percentiles, FMCSA safety, benefit prevalence, and operational performance. YANKEE FREIGHT SYSTEMS LLC leads with an average gross weekly revenue of $5,491 and an average $2,000 sign-on bonus. AD EXPRESS TRUCKING LLC follows at $2,600/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 May 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 | $7,230 | $5,399 | +34% |
| Riders-allowed policies | 90% | 79% | +11 pt |
Source: Lanefinder index, May 2026
Among the figures above, average weekly pay is where Sheboygan, Wisconsin differs most from Wisconsin — 34% above statewide.
Sheboygan, Wisconsin's top owner-operator carriers right now
The top of the list is YANKEE FREIGHT SYSTEMS LLC at $5,491/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1YANKEE FREIGHT SYSTEMS LLC — $5,491/wk
YANKEE FREIGHT SYSTEMS LLC tops the Sheboygan, Wisconsin ranking with the strongest composite score across pay, safety, benefits, and operational signals. On hours-of-service compliance, the carrier ranks in the 98th percentile per FMCSA SAFER data. Lanefinder's application data flags YANKEE FREIGHT SYSTEMS LLC as a responsive employer.
#2AD EXPRESS TRUCKING LLC — $2,600/wk
AD EXPRESS TRUCKING LLC responds to driver applications more reliably than the Sheboygan, Wisconsin median. Pay is guaranteed on a weekly minimum.
AD EXPRESS TRUCKING LLC stands alone in Sheboygan, Wisconsin's top 10 on guaranteed pay — every other ranked carrier here pays per-mile or per-load.
#3D-LINE TRUCKING INC — $5,750/wk
D-LINE TRUCKING INC responds to driver applications more reliably than the Sheboygan, Wisconsin median.
Also in the top 10: #4 WIDER GROUP INC at $6,250/wk, #5 TAZ TRUCKING INC at $10,999/wk, #6 Zmile Inc at $2,175/wk, #7 SWEET EXPRESS LLC at $8,500/wk, #8 INLAND EMPIRE LLC at $7,875/wk, #9 Ali Star Inc at $10,000/wk, #10 BLUE LIGHTNING LOGISTICS at $7,000/wk.
What Sheboygan, Wisconsin drivers actually run
8% of Sheboygan, Wisconsin's active CDL postings are regional and 91% are OTR; local plus semi-local accounts for the rest (1%).
Across Sheboygan, Wisconsin CDL postings: 1% with guaranteed pay, 26% 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 May 2026.