Updated September 2026
Best Owner-Operator Companies in Medford, Oregon (September 2026)
277 owner-operator carriers are hiring in Medford, Oregon this September 2026. WINNERS TRANSPORTATION LLC leads with an average gross weekly revenue of $2,657 and an average $2,142 sign-on bonus. WESTERN MOUNTAIN TRANSPORT INC follows at $8,500/week gross. Oregon freight moves on I-5 north-south through Portland and Eugene, with the Port of Portland handling bulk grain and auto imports, and agricultural and forestry exports — wheat, hay, lumber — generating significant outbound volumes.
What changed in September 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Where owner-operator pay is strongest in Medford, Oregon this month
The top of the list is WINNERS TRANSPORTATION LLC at $2,657/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC is number-one in Medford, Oregon this month on the composite ranking. Top FMCSA dimension here is driver fitness, in the 92nd percentile. WINNERS TRANSPORTATION LLC tracks as a responsive employer on application-response data.
#2WESTERN MOUNTAIN TRANSPORT INC — $8,500/wk
WESTERN MOUNTAIN TRANSPORT INC sits in the 93rd percentile for gross weekly revenue among Medford, Oregon carriers. WESTERN MOUNTAIN TRANSPORT INC's top FMCSA dimension is driver fitness, in the 93rd percentile. Driver applications get a faster-than-median response in Medford, Oregon.
#3Rickman Transport, LLC — $9,250/wk
Rickman Transport, LLC sits in the 96th percentile for gross weekly revenue among Medford, Oregon carriers. Rickman Transport, LLC ranks in the 91st percentile for unsafe-driving avoidance on FMCSA SAFER data.
Rickman Transport, LLC offers the highest sign-on bonus among Medford, Oregon's top 10 — $6,000.
Also in the top 10: #4 Always Franklin LLC at $8,250/wk, #5 Ali Star Inc at $10,000/wk, #6 GNS TRUCKING INC at $9,000/wk, #7 COMMONWEALTH TRANSPORTATION LLC at $4,366/wk, #8 BLUE LIGHTNING LOGISTICS at $7,000/wk, #9 LOAD MONSTER INC at $2,450/wk, #10 KILO METER LOGISTIC INC at $7,500/wk.
How drivers spend their time on the road in Medford, Oregon
9% of Medford, Oregon's active CDL postings are regional and 90% are OTR; local plus semi-local accounts for the rest (1%).
Across Medford, Oregon CDL postings: 2% with guaranteed pay, 30% dedicated, 91% take-truck-home, 72% pet-friendly, 70% riders-allowed.
Where Medford, Oregon differs from the Oregon baseline
| Medford, Oregon | Oregon top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,919 | $6,609 | +5% |
| Dedicated routes | 40% | 46% | -6 pt |
| Riders-allowed policies | 94% | 88% | +6 pt |
Source: Lanefinder index, September 2026
Medford, Oregon's biggest divergence from Oregon is on dedicated routes, 6 points below the state baseline.
Driving CDL in Oregon
Oregon freight moves on I-5 north-south through the Willamette Valley (Portland-Salem-Eugene), with the Port of Portland handling bulk grain (one of the largest US wheat-export terminals) and auto imports. Agricultural and forestry exports — wheat, hay, lumber, Christmas trees in season — generate significant outbound volume. Mountain passes on I-84 east and on US-26 west of Mt. Hood are winter operational variables. Oregon has no general sales tax but a high graduated state income tax. Cost of living in Portland is high; rural OR is more affordable.
Related guides
- Best trucking companies in Medford, Oregon
- CDL driver salary in Medford, Oregon
- Best owner-operator companies in Oregon
How we compile these rankings
Compensation is the largest single weight at 30% — pay percentile, sign-on bonus, guaranteed-pay availability, and settlement cadence. FMCSA safety contributes 25%, built from five SAFER dimensions with unsafe-driving and hours-of-service weighted 2× heavier. Benefits contribute 25%, scored separately for W2 versus owner-operator and 1099 carriers. Operational performance — application responsiveness and fleet scale — contributes 20%. Updated September 2026.