Updated July 2026
Best Owner-Operator Companies in Greenfield, Wisconsin (July 2026)
There are 619 owner-operator carriers currently posting jobs in Greenfield, Wisconsin. The ranking below reflects active jobs as of July 2026, not historical pay surveys. 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.
Greenfield, Wisconsin vs Wisconsin: the numbers that diverge
| Greenfield, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,098 | $5,295 | +15% |
| Riders-allowed policies | 86% | 78% | +8 pt |
| Pet-friendly fleets | 84% | 78% | +6 pt |
Source: Lanefinder index, July 2026
The largest gap is on average weekly pay: Greenfield, Wisconsin sits 15% above the Wisconsin baseline.
Where owner-operator pay is strongest in Greenfield, Wisconsin this month
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 is number-one in Greenfield, Wisconsin this month on the composite ranking. ROLLING ON WHEELS LLC's FMCSA score is strongest on driver fitness — 96th percentile. Driver applications get a faster-than-median response in Greenfield, Wisconsin.
#2WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC's FMCSA score is strongest on hours-of-service compliance — 96th percentile. WINNERS TRANSPORTATION LLC responds to driver applications more reliably than the Greenfield, Wisconsin median.
#3INLAND EMPIRE LLC — $7,875/wk
INLAND EMPIRE LLC pays above the 84th percentile on gross weekly revenue for the Greenfield, 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 OVERLOG INC at $3,613/wk, #7 WIDER GROUP INC at $6,250/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.
Lane mix and benefits across Greenfield, Wisconsin
9% of Greenfield, 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 Greenfield, 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 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 July 2026.