Updated September 2026
Best Owner-Operator Companies in Wauwatosa, Wisconsin (September 2026)
Lanefinder's index counts 618 active owner-operator carriers in Wauwatosa, 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.
Wauwatosa, Wisconsin vs Wisconsin: the numbers that diverge
| Wauwatosa, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,460 | $5,277 | +22% |
| Riders-allowed policies | 90% | 80% | +10 pt |
Source: Lanefinder index, September 2026
The largest gap is on average weekly pay: Wauwatosa, Wisconsin sits 22% above the Wisconsin baseline.
The owner-operator carriers leading Wauwatosa, 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 is number-one in Wauwatosa, Wisconsin this month on the composite ranking. RAY'S TRANSPORT INC pays above the 89th percentile on gross weekly revenue for the Wauwatosa, Wisconsin market. RAY'S TRANSPORT INC's FMCSA score is strongest on driver fitness — 87th percentile. RAY'S TRANSPORT INC responds to driver applications more reliably than the Wauwatosa, Wisconsin median.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC ranks in the 92nd percentile for driver fitness on FMCSA SAFER data. WINNERS TRANSPORTATION LLC tracks as a responsive employer on application-response data.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC's top FMCSA dimension is hours-of-service compliance, in the 96th percentile. Application-response data flags this carrier as a responsive employer.
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.
Lane mix and benefits across Wauwatosa, Wisconsin
The route mix in Wauwatosa, Wisconsin this month tilts OTR: 9% regional, 90% OTR, 1% local, 0% semi-local — drawn from active postings, not historical surveys.
Across Wauwatosa, Wisconsin CDL postings: 2% with guaranteed pay, 28% dedicated, 92% take-truck-home, 74% pet-friendly, 70% 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 Wauwatosa, Wisconsin
- CDL driver salary in Wauwatosa, Wisconsin
- Best owner-operator companies in Wisconsin
How we compile these rankings
Compensation is the largest single weight at 30% — pay percentile, sign-on bonus, guaranteed-pay availability, and settlement cadence. FMCSA safety contributes 25%, built from five SAFER dimensions with unsafe-driving and hours-of-service weighted 2× heavier. Benefits contribute 25%, scored separately for W2 versus owner-operator and 1099 carriers. Operational performance — application responsiveness and fleet scale — contributes 20%. Updated September 2026.