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Otr Owner Operator Jobs in Kentucky (NOW HIRING)

Diamond Transportation

Signing: OTR Owner Operators (Accepting Independent Contractors W/ Trucks), MUST HAVE RGN, FLATBED OR STEPDECK EXPERIENCE with good knowledge of chaining, strapping and securement! Company info:

STG Logistics

Owner Operator

Elizabethtown, KY · On-site

... on the road. Whether you're running port containers daily or looking to grow your intermodal business, STG Drayage offers long-term opportunity with consistent freight volumes. Owner-Operator ...

STG Logistics

Owner Operator

Louisville, KY · On-site

... on the road. Whether you're running port containers daily or looking to grow your intermodal business, STG Drayage offers long-term opportunity with consistent freight volumes. Owner-Operator ...

STG Logistics

Owner Operator

Shepherdsville, KY · On-site

... on the road. Whether you're running port containers daily or looking to grow your intermodal business, STG Drayage offers long-term opportunity with consistent freight volumes. Owner-Operator ...

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Showing results 21-40

All JobsOtr Owner Operator JobsOtr Owner Operator Jobs in Kentucky

Otr Owner Operator information

See Kentucky salary details

$926

$5.5K

$6.7K

How much do otr owner operator jobs pay per week?

As of Aug 22, 2026, the average weekly pay for otr owner operator in Kentucky is $5,509.37, according to ZipRecruiter salary data. Most workers in this role earn between $5,846.15 and $5,846.15 per week, depending on experience, location, and employer.

What is an OTR owner operator?

An OTR (Over-the-Road) Owner Operator is a self-employed truck driver who owns and operates their own semi-truck to transport goods over long distances. They contract with freight companies or shippers to haul loads across state lines, often spending weeks on the road. Unlike company drivers, they are responsible for expenses such as fuel, maintenance, and insurance, but they also have the potential to earn higher profits. OTR Owner Operators have greater flexibility in choosing their routes and schedules, but they must also manage business aspects like bookkeeping and compliance with regulations.

What are some common challenges faced by OTR owner operators and how can they be managed?

One of the main challenges OTR Owner Operators encounter is managing long periods away from home while balancing tight delivery schedules and maintaining their equipment. Dealing with unexpected breakdowns, variable fuel costs, and strict regulatory compliance can also add pressure to the role. Staying organized, planning routes efficiently, and budgeting carefully help manage both operational and personal challenges. Many successful owner operators also join supportive carrier networks and leverage professional resources for ongoing maintenance and business guidance.

What are the key skills and qualifications needed to thrive in the OTR owner operator position, and why are they important?

To thrive as an OTR (Over-The-Road) Owner Operator, you need a valid commercial driver’s license (CDL), extensive long-haul driving experience, and a strong understanding of DOT regulations and safe driving practices. Familiarity with GPS navigation systems, electronic logging devices (ELDs), and routine truck maintenance is crucial. Excellent time management, self-motivation, and communication skills help independent operators manage schedules and client relationships effectively. These competencies are essential for ensuring safety, timely deliveries, legal compliance, and profitable business operations on extended routes.

What are popular job titles related to Otr Owner Operator jobs in Kentucky?

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What job categories do people searching Otr Owner Operator jobs in Kentucky look for?

The top searched job categories for Otr Owner Operator jobs in Kentucky are:

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Otr Owner Operator jobs near you
Infographic showing various Otr Owner Operator job openings in Kentucky as of August 2026, with employment types broken down into 45% Full Time, 52% Part Time, 2% Contract, and 1% Nights. Highlights an 98% Physical, and 2% Remote job distribution, with an average salary of $286,487 per year, or $137.7 per hour.

Class A CDL Owner Operator - 2yrs EXP Required - OTR - Diamond Transportation

Diamond Transportation

Louisville, KY

Full-time

Re-posted 6 days ago

Job description

Diamond Transportation Signing OTR Owner Operators .

Signing: OTR Owner Operators (Accepting Independent Contractors W/ Trucks), MUST HAVE RGN, FLATBED OR STEPDECK EXPERIENCE with good knowledge of chaining, strapping and securement!


Company info:

Diamond Transportation System, Inc. has a rich history of pioneering the transportation of farm equipment and tractors starting in the 1940’s and expanded to the 100% Owner Operator Company with a Fortune 500 customer base that it is today. From humble beginnings to now serving the U.S. and Canada – transportation of Agricultural and Construction Equipment along with various types of Machinery is our specialty and our dedication to our customers and our contractors will carry us well into the next millennium.

Job Details:

  • Diamond has been in business for over 80 years.
  • Competitive pay
  • Weekly or Daily settlements – your choice
  • Personal ‘Guardian’ Fleet Manager to understand your individual needs
  • Non-forced Dispatch
  • Looking for Owner Operators with ‘open-deck’ experience to haul Flatbed, StepDeck, RGN (Removable Gooseneck) Trailers” ONLY!! 
  • Compensation packages include:
  • Percentage pay
  • Additional percent with your own trailer
  • Quarterly Safety Compensation
  • Referral compensation up to $2,500
  • No Trailer Rent
  • No Permit fees – we pay for the OD permits and you give us your routes
  • Sign on compensation (bonus)
  • Cargo and liability insurance at no additional cost
  • Available competitive insurance offerings for:
  • Physical Damage
  • Occupational Accident
  • NOTC/Bobtail
  • Passenger Authorization
  • Medical
  • License plate escrow (if plate needed)
  • Customer referral program
  • In-cab communications
  • ELD ready
  • Fuel card
  • Company RGN trailers
  • Fuel tax reporting
  • Fuel Discount Program
  • Tire Discount Program
  • We have Owner Operators just like YOU, leased to us for over 30 years.
  • Our family owned and operated company has only one concern, YOUR success as an Owner Operator.
  • We have the experience, the customer base and the freight to keep you making money.
  • Bottom Line…if YOU are successful, then we are successful.
  • It’s a partnership! We’re A 100% Owner Operator Company You won’t have any company trucks to compete with here!


Job Requirements:

  • MUST HAVE RGN, FLATBED & STEPDECK EXPERIENCE with good knowledge of chaining, strapping and securement!
  • If you can answer yes to these questions… Are at least 23 years old?
  • Does your background include six months of machinery / heavy haul / over-dimensional experience?
  • Do you have a good driving record?
  • Do you have a solid work history?
  • Can your truck pass a D.O.T. inspection

Apply