Updated September 2026
Best Owner-Operator Companies in Waukesha, Wisconsin (September 2026)
Lanefinder's index counts 622 active owner-operator carriers in Waukesha, Wisconsin this September 2026. 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.
Where Waukesha, Wisconsin differs from the Wisconsin baseline
| Waukesha, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,473 | $5,277 | +23% |
| Riders-allowed policies | 88% | 80% | +8 pt |
Source: Lanefinder index, September 2026
Waukesha, Wisconsin's biggest divergence from Wisconsin is on average weekly pay, 23% above the state baseline.
Where owner-operator pay is strongest in Waukesha, Wisconsin this month
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 leads the Waukesha, Wisconsin market on combined gross revenue and ranking score this month. RAY'S TRANSPORT INC's gross weekly revenue ranks in the 95th percentile across Waukesha, Wisconsin. RAY'S TRANSPORT INC ranks in the 87th percentile for driver fitness on FMCSA SAFER data. Application-response data flags this carrier as a responsive employer.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC's FMCSA score is strongest on driver fitness — 92nd percentile. Lanefinder's application data flags WINNERS TRANSPORTATION LLC as a responsive employer.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC's FMCSA score is strongest on hours-of-service compliance — 96th percentile. Driver applications get a faster-than-median response in Waukesha, Wisconsin.
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 POPE TRANSPORT INC at $7,000/wk, #9 BLUE LIGHTNING LOGISTICS at $7,000/wk, #10 C & G TRANSPORTATION INC at $7,500/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 28%; take-truck-home at 92%. Pet-friendly policies appear at 74% and riders-allowed at 69%.
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 September 2026.