Updated July 2026
Best Owner-Operator Companies in Waukesha, Wisconsin (July 2026)
Lanefinder's index counts 617 active owner-operator carriers in Waukesha, Wisconsin this July 2026. 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.
Where Waukesha, Wisconsin differs from the Wisconsin baseline
| Waukesha, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,203 | $5,254 | +18% |
| Riders-allowed policies | 84% | 78% | +6 pt |
| Dedicated routes | 56% | 51% | +5 pt |
Source: Lanefinder index, July 2026
Waukesha, Wisconsin's biggest divergence from Wisconsin is on average weekly pay, 18% above the state baseline.
Where owner-operator pay is strongest in Waukesha, Wisconsin this month
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 Waukesha, Wisconsin this month on the composite ranking. ROLLING ON WHEELS LLC's top FMCSA dimension is driver fitness, in the 96th percentile. ROLLING ON WHEELS LLC responds to driver applications more reliably than the Waukesha, Wisconsin median.
#2WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC's FMCSA score is strongest on hours-of-service compliance — 96th percentile. Lanefinder's application data flags WINNERS TRANSPORTATION LLC as a responsive employer.
#3INLAND EMPIRE LLC — $7,875/wk
INLAND EMPIRE LLC pays above the 84th percentile on gross weekly revenue for the Waukesha, 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 WIDER GROUP INC at $6,250/wk, #7 OVERLOG INC at $3,613/wk, #8 BLUE LIGHTNING LOGISTICS at $7,000/wk, #9 POPE TRANSPORT INC at $7,000/wk, #10 BB8 FREIGHT CO at $12,666/wk.
How drivers spend their time on the road in Waukesha, Wisconsin
9% of Waukesha, Wisconsin's active CDL postings are regional and 90% are OTR; local plus semi-local accounts for the rest (1%).
Guaranteed pay is on offer at 2% of Waukesha, Wisconsin postings; dedicated routes at 27%; take-truck-home at 92%. Pet-friendly policies appear at 75% and riders-allowed at 70%.
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 Waukesha, Wisconsin
- CDL driver salary in Waukesha, Wisconsin
- Best owner-operator companies in Wisconsin
Where this data comes from
Rankings combine four signals: compensation (30%) including pay percentile, sign-on bonuses, guaranteed pay, and settlement frequency; FMCSA safety (25%); benefits (25%) scored differently for W2 vs owner-operator carriers; and operational performance (20%) measuring employer responsiveness and fleet scale. Recomputed monthly from real active job postings. Updated July 2026.