Updated September 2026
Best Owner-Operator Companies in Cleveland, Ohio (September 2026)
652 owner-operator carriers are hiring in Cleveland, Ohio this September 2026. 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. Cleveland anchors I-90 on Lake Erie with a major port handling bulk commodities (iron ore, limestone, cement, salt), and the I-71 / I-77 / I-90 grid connects automotive manufacturing, steel, and chemical corridor loads across northeast Ohio.
What changed in September 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
The owner-operator carriers leading Cleveland, Ohio this month
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 Cleveland, Ohio ranking with the strongest composite score across pay, safety, benefits, and operational signals. The carrier ranks in the 95th percentile for gross weekly revenue in Cleveland, Ohio. RAY'S TRANSPORT INC ranks in the 87th percentile for driver fitness on FMCSA SAFER data. The carrier tracks as a responsive employer on Lanefinder's data.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC's top FMCSA dimension is driver fitness, in the 92nd percentile. WINNERS TRANSPORTATION LLC responds to driver applications more reliably than the Cleveland, Ohio median.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC's top FMCSA dimension is hours-of-service compliance, in the 96th percentile. Lanefinder's application data flags LOAD MONSTER INC as a responsive employer.
Also in the top 10: #4 WESTERN MOUNTAIN TRANSPORT INC at $8,750/wk, #5 B & T EXPRESS INC at $6,750/wk, #6 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #7 WIDER GROUP INC at $6,250/wk, #8 POPE TRANSPORT INC at $7,000/wk, #9 BLUE LIGHTNING LOGISTICS at $7,000/wk, #10 KILO METER LOGISTIC INC at $7,500/wk.
What Cleveland, Ohio drivers actually run
Of active CDL postings in Cleveland, Ohio this month, 11% are regional and 88% are OTR (long-haul). Local and semi-local routes account for the remaining 1%.
Guaranteed pay is on offer at 2% of Cleveland, Ohio postings; dedicated routes at 28%; take-truck-home at 91%. Pet-friendly policies appear at 72% and riders-allowed at 69%.
Where Cleveland, Ohio differs from the Ohio baseline
The largest gap is on average weekly pay: Cleveland, Ohio sits 3% above the Ohio baseline.
Driving CDL in Ohio
Ohio sits at the center of the US manufacturing belt and runs about as much through-freight as any state. I-70, I-71, I-75, and the Ohio Turnpike form a freight grid that's flat, generally well-maintained, and forgiving for newer drivers — Ohio is one of the better states to gain initial OTR experience. The Cleveland, Columbus, and Cincinnati metros each anchor distinct lane profiles (auto, distribution, and pharmaceutical respectively). Winter operational risk is real — lake-effect off Erie, freezing rain in the central part of the state — but less extreme than the Great Plains states. Ohio cost of living is below the national average, which makes the income math work better than the headline pay numbers suggest.
Related guides
- Best trucking companies in Cleveland, Ohio
- CDL driver salary in Cleveland, Ohio
- Best owner-operator companies in Ohio
The methodology behind the rankings
Rankings combine four signals: compensation (30%) including pay percentile, sign-on bonuses, guaranteed pay, and settlement frequency; FMCSA safety (25%); benefits (25%) scored differently for W2 vs owner-operator carriers; and operational performance (20%) measuring employer responsiveness and fleet scale. Recomputed monthly from real active job postings. Updated September 2026.