Updated September 2026
Best Owner-Operator Companies in Greenfield, Wisconsin (September 2026)
There are 624 owner-operator carriers currently posting jobs in Greenfield, Wisconsin. The ranking below reflects active jobs as of September 2026, not historical pay surveys. 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.
Greenfield, Wisconsin vs Wisconsin: the numbers that diverge
| Greenfield, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,393 | $5,277 | +21% |
| Riders-allowed policies | 88% | 80% | +8 pt |
Source: Lanefinder index, September 2026
The largest gap is on average weekly pay: Greenfield, Wisconsin sits 21% above the Wisconsin baseline.
Where owner-operator pay is strongest in Greenfield, 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 Greenfield, Wisconsin this month on the composite ranking. RAY'S TRANSPORT INC's gross weekly revenue ranks in the 95th percentile across Greenfield, Wisconsin. Top FMCSA dimension here is driver fitness, in the 87th percentile. The carrier tracks as a responsive employer on Lanefinder's data.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC's FMCSA score is strongest on driver fitness — 92nd percentile. WINNERS TRANSPORTATION LLC responds to driver applications more reliably than the Greenfield, Wisconsin median.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC ranks in the 96th percentile for hours-of-service compliance on FMCSA SAFER data. Lanefinder's application data flags LOAD MONSTER INC 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 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 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 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 September 2026.