Updated July 2026
Best Owner-Operator Companies in Madison, Wisconsin (July 2026)
As of July 2026, 604 carriers in Madison, Wisconsin are posting active jobs for owner-operators. ROLLING ON WHEELS LLC leads with an average gross weekly revenue of $5,500. WINNERS TRANSPORTATION LLC follows at $2,437/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 July 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 | $6,390 | $5,295 | +21% |
| Sign-on bonus rate | 26% | 32% | -6 pt |
| Riders-allowed policies | 88% | 78% | +10 pt |
Source: Lanefinder index, July 2026
Among the figures above, average weekly pay is where Madison, Wisconsin differs most from Wisconsin — 21% above statewide.
Madison, Wisconsin's top owner-operator carriers right now
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 leads the Madison, Wisconsin market on combined gross revenue and ranking score this month. ROLLING ON WHEELS LLC's FMCSA score is strongest on driver fitness — 96th percentile. Driver applications get a faster-than-median response in Madison, Wisconsin.
#2WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC ranks in the 96th percentile for hours-of-service compliance on FMCSA SAFER data. WINNERS TRANSPORTATION LLC responds to driver applications more reliably than the Madison, Wisconsin median.
#3INLAND EMPIRE LLC — $7,875/wk
INLAND EMPIRE LLC pays above the 84th percentile on gross weekly revenue for the Madison, Wisconsin market.
Also in the top 10: #4 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #5 OVERLOG INC at $3,613/wk, #6 WIDER GROUP INC at $6,250/wk, #7 BLUE LIGHTNING LOGISTICS at $7,000/wk, #8 POPE TRANSPORT INC at $7,000/wk, #9 BB8 FREIGHT CO at $12,666/wk, #10 DAHL TRUCKING LLC at $3,750/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 26%; 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 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 July 2026.