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Owner Operator Contractor Jobs in Cleveland, OH (NOW HIRING)

Clark Transfer Inc

CDL A Owner Operator

Painesville, OH

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Medina, OH

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Elyria, OH

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Mentor, OH

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

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Showing results 1-20

All JobsOwner Operator Contractor JobsOwner Operator Contractor Jobs in Cleveland, OH

Owner Operator Contractor information

See Cleveland, OH salary details

$624

$4.3K

$7.5K

How much do owner operator contractor jobs pay per week?

As of Aug 19, 2026, the average weekly pay for owner operator contractor in Cleveland, OH is $4,263.06, according to ZipRecruiter salary data. Most workers in this role earn between $2,330.77 and $6,340.38 per week, depending on experience, location, and employer.

What is an owner operator contractor?

Owner Operator Contractors are self-employed individuals or businesses who own and operate their own vehicles or equipment to provide transportation or delivery services. They typically contract with larger companies or clients to haul goods, manage logistics, or perform specialized tasks, often in the trucking or freight industry. As independent contractors, they are responsible for maintaining their equipment, managing expenses, and complying with regulations. This role offers greater flexibility and profit potential but also comes with higher risks and responsibilities compared to company-employed drivers.

What are some common challenges owner operator contractors face when managing their own business?

Owner Operator Contractors often face challenges related to balancing driving duties with the administrative responsibilities of running a business. Tasks such as handling contracts, maintaining equipment, managing finances, and securing consistent loads can require significant time and attention. Additionally, they are responsible for compliance with safety regulations and industry standards, which can be complex and ever-changing. Many find that building relationships with brokers and shippers is essential for steady work, and effective time management is key to maintaining profitability.

What are the key skills and qualifications needed to thrive as an owner operator contractor, and why are they important?

To thrive as an Owner Operator Contractor, you need a valid commercial driver's license (CDL), a clean driving record, and business management knowledge. Familiarity with electronic logging devices (ELDs), GPS systems, and compliance with Department of Transportation (DOT) regulations is essential. Strong organizational skills, self-motivation, and effective communication set top performers apart in managing routes and client relationships. These skills ensure safe, efficient operations and sustainable business growth in the competitive logistics industry.

What is the difference between Owner Operator Contractor vs Truck Driver?

AspectOwner Operator ContractorTruck Driver
CredentialsCommercial Driver's License (CDL), business registrationCommercial Driver's License (CDL)
Work EnvironmentOwn truck, independent, flexible scheduleCompany-owned trucks, fixed routes, employer-managed
Employer/Industry UsageSelf-employed or contracted with carriersEmployed by trucking companies
Search/Comparison IntentHigh overlap in responsibilities and credentialsDifferent in independence and employment status

In summary, Owner Operator Contractors own and operate their trucks independently, often contracting with carriers, while Truck Drivers are typically employed by companies and operate company-owned vehicles. Both roles require a CDL, but their work setup and employment status differ significantly.

What are popular job titles related to Owner Operator Contractor jobs in Cleveland, OH?

For Owner Operator Contractor jobs in Cleveland, OH, the most frequently searched job titles are:

What job categories do people searching Owner Operator Contractor jobs in Cleveland, OH look for?

The top searched job categories for Owner Operator Contractor jobs in Cleveland, OH are:

What cities near Cleveland, OH are hiring for Owner Operator Contractor jobs?

Cities near Cleveland, OH with the most Owner Operator Contractor job openings:

Owner Operator Contractor jobs near you
Infographic showing various Owner Operator Contractor job openings in Cleveland, OH as of August 2026, with employment types broken down into 45% Full Time, 51% Part Time, 3% Contract, and 1% Nights. Highlights an 99% Physical, and 1% Remote job distribution, with an average salary of $221,679 per year, or $106.6 per hour.

Truck drivers/Owner-Operator/Contractors

Five Star Trucking, Inc

Willoughby, OH • On-site

Full-time

Re-posted 21 days ago

Job description

Company Description
Five Star is a winning team. Our people are outstanding and have proven themselves. Our responsible dispatchers are in 24-hour contact with our reliable drivers, allowing us to follow the progress of all shipments. We provide the best service available and our growth and customer loyalty has proven it. Our team cooperation, along with reliability, makes Five Star a viable choice for shippers. We welcome you to Five Star. We have what it takes! We have the people...we have the equipment! Don't hesitate, join a winning team! Call now! (440) 953-9300 or 1-800-231-3658.
• OPERATING AUTHORITY
We are an irregular route common carrier, a contract carrier, and have Ohio Intrastate Authority. We complete our versatility with a proper broker's license.
• OPERATIONS
Our drivers are in contact daily with our central dispatch allowing us to plan for their next load. We know where the loads are at all times. Our operations run 24 hours around the clock, 7 days a week. We offer 48' and 53' vans and reefers. We offer city service as well as warehousing to accommodate our customers needs.
Job Description
FIVE STAR TRUCKING INC. is now hiring OWNER OPERATORS and SMALL FLEET OWNERS in WILLOUGHY, OH (17 miles east of Cleveland) for regional short and long haul runs. Our company has been in transportation for over 35 years, family owned, financially stable and continuing to provide quality service to our own network of shippers. We seek the best owner operators to join an excellent team of single and team operators.
Be part of our company family and enjoy:
  • Excellent Home time
  • Fuel Surcharge
  • Stable customer base
  • Safe work environment
  • Opportunity for growth and expansion
  • Enormous amount of work available
  • No forced Dispatch
  • Excellent pay

If you looking for a rewarding opportunity, a company that cares about its contractors, you've come to the right place! FIVE STAR TRUCKING INC has been a leader in the transportation industry for over 35 years.
We have immediate openings for Owner Operators/Teams
Call Five Star Safety for more information: 1-800-321-3658 or 440-953-9300.
Qualifications
  • All applicants must have atleast 3 years of experience driving
  • All applicants must have a valid class A CDL.
  • Any owner operators with their own truck and/or trailer mus be able to pass inspection

Additional Information
All your information will be kept confidential according to EEO guidelines.

Apply