Updated September 2026
Best Owner-Operator Companies in Madison, Wisconsin (September 2026)
As of September 2026, 609 carriers in Madison, Wisconsin are posting active jobs for owner-operators. 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. Madison sits at the I-90 / I-94 junction in south-central Wisconsin, with large-scale dairy and food processing, university institutional procurement, and manufacturing distribution for the Wisconsin River Valley corridor.
What changed in September 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Madison, Wisconsin vs Wisconsin: the numbers that diverge
| Madison, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,569 | $5,277 | +24% |
| Riders-allowed policies | 90% | 80% | +10 pt |
| Dedicated routes | 48% | 42% | +6 pt |
Source: Lanefinder index, September 2026
Among the figures above, average weekly pay is where Madison, Wisconsin differs most from Wisconsin — 24% above statewide.
Madison, Wisconsin's top owner-operator carriers right now
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 tops the Madison, Wisconsin ranking with the strongest composite score across pay, safety, benefits, and operational signals. Gross weekly revenue here lands in the 94th percentile across Madison, Wisconsin. Top FMCSA dimension here is driver fitness, in the 87th percentile. Application-response data flags this carrier as a responsive employer.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC ranks in the 92nd percentile for driver fitness on FMCSA SAFER data. WINNERS TRANSPORTATION LLC responds to driver applications more reliably than the Madison, 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. Driver applications get a faster-than-median response in Madison, Wisconsin.
Also in the top 10: #4 WESTERN MOUNTAIN TRANSPORT INC at $8,750/wk, #5 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #6 WIDER GROUP INC at $6,250/wk, #7 POPE TRANSPORT INC at $7,000/wk, #8 BLUE LIGHTNING LOGISTICS at $7,000/wk, #9 Ali Star Inc at $10,000/wk, #10 C & G TRANSPORTATION INC at $7,500/wk.
How drivers spend their time on the road in Madison, Wisconsin
7% of Madison, Wisconsin's active CDL postings are regional and 92% are OTR; local plus semi-local accounts for the rest (1%).
Guaranteed pay is on offer at 2% of Madison, Wisconsin postings; dedicated routes at 27%; take-truck-home at 93%. Pet-friendly policies appear at 74% 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 Madison, Wisconsin
- CDL driver salary in Madison, Wisconsin
- Best owner-operator companies in Wisconsin
How we compile these rankings
Four weighted components. Compensation carries 30% and includes pay percentile, sign-on bonus tier, guaranteed-pay availability, and settlement frequency. FMCSA safety carries 25%, built from five SAFER dimensions. Benefits carry 25%, scored separately for W2 versus owner-operator carriers. Operational performance carries 20%, measuring application responsiveness and fleet scale. Updated September 2026.