Updated July 2026
Best Owner-Operator Companies in Brookfield, Wisconsin (July 2026)
616 owner-operator carriers are hiring in Brookfield, 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.
Brookfield, Wisconsin vs Wisconsin: the numbers that diverge
| Brookfield, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,273 | $5,295 | +18% |
| Riders-allowed policies | 84% | 78% | +6 pt |
Source: Lanefinder index, July 2026
The largest gap is on average weekly pay: Brookfield, Wisconsin sits 18% above the Wisconsin baseline.
Brookfield, 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 Brookfield, Wisconsin market on combined gross revenue and ranking score this month. ROLLING ON WHEELS LLC's FMCSA score is strongest on driver fitness — 96th percentile. Lanefinder's application data flags ROLLING ON WHEELS LLC as a responsive employer.
#2WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC ranks in the 96th percentile for hours-of-service compliance on FMCSA SAFER data. Driver applications get a faster-than-median response in Brookfield, Wisconsin.
#3INLAND EMPIRE LLC — $7,875/wk
INLAND EMPIRE LLC pays above the 84th percentile on gross weekly revenue for the Brookfield, 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 Brookfield, Wisconsin
9% of Brookfield, 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 Brookfield, 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 Brookfield, Wisconsin
- CDL driver salary in Brookfield, Wisconsin
- Best owner-operator companies in Wisconsin
How we compile these rankings
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.