Updated September 2026
Best Owner-Operator Companies in Lake Oswego, Oregon (September 2026)
438 owner-operator carriers are currently posting jobs in Lake Oswego, Oregon as of 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 Lake Oswego, 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 Lake Oswego, Oregon this month on the composite ranking. WINNERS TRANSPORTATION LLC's FMCSA score is strongest on driver fitness — 92nd percentile. Driver applications get a faster-than-median response in Lake Oswego, Oregon.
#2WESTERN MOUNTAIN TRANSPORT INC — $8,500/wk
WESTERN MOUNTAIN TRANSPORT INC sits in the 94th percentile for gross weekly revenue among Lake Oswego, Oregon carriers. Top FMCSA dimension here is driver fitness, in the 93rd percentile. WESTERN MOUNTAIN TRANSPORT INC tracks as a responsive employer on application-response data.
#3Rickman Transport, LLC — $9,250/wk
Rickman Transport, LLC sits in the 96th percentile for gross weekly revenue among Lake Oswego, Oregon carriers. On unsafe-driving avoidance, the carrier ranks in the 91st percentile per FMCSA SAFER data.
For sign-on cash, Rickman Transport, LLC posts the largest bonus in Lake Oswego, Oregon's top 10 at $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.
Lane mix and benefits across Lake Oswego, Oregon
Of active CDL postings in Lake Oswego, Oregon this month, 8% are regional and 91% are OTR (long-haul). Local and semi-local routes account for the remaining 1%.
Guaranteed pay is on offer at 1% of Lake Oswego, Oregon postings; dedicated routes at 27%; take-truck-home at 92%. Pet-friendly policies appear at 73% and riders-allowed at 72%.
Lake Oswego, Oregon vs Oregon: the numbers that diverge
Lake Oswego, 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 Lake Oswego, Oregon
- CDL driver salary in Lake Oswego, Oregon
- Best owner-operator companies in Oregon
How we compile these rankings
Carriers are scored against carriers in their own market. The composite is 30% compensation (pay + bonus + guaranteed pay + settlement cadence), 25% FMCSA safety, 25% benefits (W2 vs owner-op scoring), and 20% operational performance (responsiveness + fleet scale). No paid placement — the weights are the same for every carrier in the index. Updated September 2026.