Updated September 2026
Best Owner-Operator Companies in Gresham, Oregon (September 2026)
Gresham, Oregon, September 2026: 438 active owner-operator carriers. 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.
Gresham, Oregon's top owner-operator carriers right now
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 tops the Gresham, Oregon ranking with the strongest composite score across pay, safety, benefits, and operational signals. Strongest FMCSA dimension is driver fitness — 92nd percentile. The carrier tracks as a responsive employer on Lanefinder's data.
#2WESTERN MOUNTAIN TRANSPORT INC — $8,500/wk
WESTERN MOUNTAIN TRANSPORT INC sits in the 94th percentile for gross weekly revenue among Gresham, Oregon carriers. On driver fitness, the carrier ranks in the 93rd percentile per FMCSA SAFER data. Lanefinder's application data flags WESTERN MOUNTAIN TRANSPORT INC as a responsive employer.
#3Rickman Transport, LLC — $9,250/wk
Rickman Transport, LLC pays above the 91st percentile on gross weekly revenue for the Gresham, Oregon market. 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 Gresham, Oregon's top 10 — $6,000.
Also in the top 10: #4 GNS TRUCKING INC at $9,000/wk, #5 Ali Star Inc at $10,000/wk, #6 BLUE LIGHTNING LOGISTICS at $7,000/wk, #7 KILO METER LOGISTIC INC at $7,500/wk, #8 C & G TRANSPORTATION INC at $7,500/wk, #9 TP TRUCKING at $8,500/wk, #10 LOAD MONSTER INC at $2,450/wk.
What Gresham, Oregon drivers actually run
Of active CDL postings in Gresham, Oregon this month, 7% are regional and 91% are OTR (long-haul). Local and semi-local routes account for the remaining 2%.
Across Gresham, Oregon CDL postings: 1% with guaranteed pay, 27% dedicated, 92% take-truck-home, 73% pet-friendly, 72% riders-allowed.
Gresham, Oregon vs Oregon: the numbers that diverge
Gresham, Oregon's biggest divergence from Oregon is on average weekly pay, 6% above 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 Gresham, Oregon
- CDL driver salary in Gresham, Oregon
- Best owner-operator companies in Oregon
Where this data comes from
The composite score is 30% compensation, 25% FMCSA safety, 25% benefits, and 20% operational performance. Pay percentiles are computed against carriers currently hiring in each market; FMCSA percentiles come from SAFER and weight unsafe-driving and hours-of-service violations 2× heavier than the other three dimensions. Updated September 2026.