Updated May 2026
Best Owner-Operator Companies in Waukesha, Wisconsin (May 2026)
Lanefinder's index counts 623 active owner-operator carriers in Waukesha, Wisconsin this May 2026. 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.
Where Waukesha, Wisconsin differs from the Wisconsin baseline
| Waukesha, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,886 | $5,399 | +28% |
| Riders-allowed policies | 86% | 79% | +7 pt |
| Dedicated routes | 53% | 48% | +5 pt |
Source: Lanefinder index, May 2026
Waukesha, Wisconsin's biggest divergence from Wisconsin is on average weekly pay, 28% above the state baseline.
Where owner-operator pay is strongest in Waukesha, Wisconsin this month
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 is number-one in Waukesha, Wisconsin this month on the composite ranking. Top FMCSA dimension here is hours-of-service compliance, in the 98th percentile. Application-response data flags this carrier as a responsive employer.
#2AD EXPRESS TRUCKING LLC — $2,600/wk
AD EXPRESS TRUCKING LLC tracks as a responsive employer on application-response data. AD EXPRESS TRUCKING LLC offers a guaranteed weekly minimum.
Among Waukesha, Wisconsin's top 10, only AD EXPRESS TRUCKING LLC pays guaranteed weekly wages — useful if route variance matters.
#3D-LINE TRUCKING INC — $5,750/wk
D-LINE TRUCKING INC responds to driver applications more reliably than the Waukesha, 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 POPE TRANSPORT INC at $7,000/wk, #10 Ali Star Inc at $10,000/wk.
How drivers spend their time on the road in Waukesha, Wisconsin
9% of Waukesha, Wisconsin's active CDL postings are regional and 89% are OTR; local plus semi-local accounts for the rest (2%).
Guaranteed pay is on offer at 1% of Waukesha, Wisconsin postings; dedicated routes at 27%; take-truck-home at 93%. 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 May 2026.