Updated May 2026
Best Owner-Operator Companies in Greenfield, Wisconsin (May 2026)
There are 625 owner-operator carriers currently posting jobs in Greenfield, Wisconsin. The ranking below reflects active jobs as of May 2026, not historical pay surveys. 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.
Greenfield, Wisconsin vs Wisconsin: the numbers that diverge
| Greenfield, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,763 | $5,399 | +25% |
| Riders-allowed policies | 86% | 79% | +7 pt |
Source: Lanefinder index, May 2026
The largest gap is on average weekly pay: Greenfield, Wisconsin sits 25% above the Wisconsin baseline.
Where owner-operator pay is strongest in Greenfield, 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 Greenfield, Wisconsin this month on the composite ranking. Strongest FMCSA dimension is hours-of-service compliance — 98th percentile. The carrier tracks as a responsive employer on Lanefinder's data.
#2AD EXPRESS TRUCKING LLC — $2,600/wk
AD EXPRESS TRUCKING LLC tracks as a responsive employer on application-response data. AD EXPRESS TRUCKING LLC runs a guaranteed-pay structure on the comp package.
Among Greenfield, Wisconsin's top 10, only AD EXPRESS TRUCKING LLC pays guaranteed weekly wages — useful if route variance matters.
#3WIDER GROUP INC — $6,250/wk
WIDER GROUP INC is active in Greenfield, Wisconsin with a current open requisition.
Also in the top 10: #4 D-LINE TRUCKING INC at $5,750/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.
Lane mix and benefits across Greenfield, Wisconsin
9% of Greenfield, 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 Greenfield, 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 Greenfield, Wisconsin
- CDL driver salary in Greenfield, Wisconsin
- Best owner-operator companies in Wisconsin
The methodology behind the rankings
Pay carriers in the same market against each other (30% of the score). Add a five-dimension FMCSA safety percentile from SAFER (25%). Score benefits based on whether the carrier hires W2 drivers or contractors (25%). Layer on employer responsiveness and fleet scale (20%). The weights are fixed and public. Updated May 2026.