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Owner Operators Jobs in Grayson, KY (NOW HIRING)

Chick-fil-A

Front of House Team Member

Ashland, KY · On-site

$11 - $14/hr

In addition to working directly for an independent Owner/Operator, Team Members gain life experience that goes far beyond serving a great product in a friendly environment. Team Members are ...

Chick-fil-A

Back of House Team Member

Ashland, KY · On-site

$11 - $14/hr

In addition to working directly for an independent Owner/Operator, Back of House Team Members gain life experience that goes far beyond serving a great product in a friendly environment. They are ...

CRH

Asphalt Plant Operator

Olive Hill, KY · On-site

Privately owned and operated until 2006, the Mountain Companies later joined CRH. By being a part of the CRH family, we are a proud reflection of the hundreds of family businesses, local and regional ...

FastSigns

Installer production

Ashland, KY · On-site

$540/wk

When you work at an independently owned and operated FASTSIGNS location, you are working for a local business, typically with Monday through Friday business hours. A work truck is provided to work ...

Wendy's

Managers Breakfast & Lunch

Ashland, KY · On-site

$12 - $15/hr

Independently owned and operated, Wendy's franchise organizations determine their own compensation, benefits and career programs which may vary from company-owned locations. Visit to apply

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All JobsOwner Operators JobsOwner Operators Jobs in Grayson, KY

Owner Operators information

See Grayson, KY salary details

$455

$3.1K

$5.4K

How much do owner operators jobs pay per week?

As of Aug 16, 2026, the average weekly pay for owner operators in Grayson, KY is $3,106.77, according to ZipRecruiter salary data. Most workers in this role earn between $1,698.08 and $4,621.15 per week, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as an owner operator?

To thrive as an Owner Operator, you need strong business management skills, a commercial driver's license (CDL), and a thorough understanding of transportation regulations and logistics. Familiarity with electronic logging devices (ELDs), freight brokerage platforms, and route planning software is often necessary. Excellent time management, self-motivation, and communication skills set standout candidates apart in this competitive field. These skills and qualities are vital to efficiently manage your own business, ensure regulatory compliance, and maintain reliable client relationships.

How do owner operators find jobs?

Owner operators find jobs through load boards, freight brokers, and direct relationships with shippers or carriers. They often use industry-specific platforms, build networks, and maintain good reputation to secure consistent work, while also managing necessary licenses and insurance requirements.

What is an owner operator?

An Owner Operator is a self-employed truck driver who owns and operates their own commercial vehicle. They either haul freight for a company under a contract or run their own independent trucking business. Responsibilities include managing expenses, securing contracts, maintaining their truck, and complying with industry regulations. Being an Owner Operator provides more control over routes and schedules but also comes with financial risks and business management responsibilities.

How much do most owner operators make?

Most owner operators in the trucking industry earn between $100,000 and $200,000 annually, depending on factors such as experience, routes, and equipment. Earnings can vary widely based on load volume, fuel costs, and operational efficiency, with some owner operators making more through specialized freight or dedicated routes.

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

Owner Operators often encounter challenges such as fluctuating fuel costs, finding consistent loads, maintaining their vehicles, and keeping up with regulatory requirements. Staying organized with digital tools for load planning and maintenance scheduling can help streamline operations. Building strong relationships with freight brokers and direct shippers may increase access to steady work, while careful budgeting can assist in managing overhead expenses. Additionally, keeping up-to-date with industry regulations can ensure your business remains compliant and operates smoothly. Addressing these challenges proactively helps promote a successful and sustainable operation.

What cities near Grayson, KY are hiring for Owner Operators jobs?

Cities near Grayson, KY with the most Owner Operators job openings:

Owner Operators jobs near you
Infographic showing various Owner Operators job openings in Grayson, KY as of August 2026, with employment types broken down into 86% Full Time, 10% Part Time, and 4% Contract. Highlights an 94% Physical, 2% Hybrid, and 4% Remote job distribution, with an average salary of $161,552 per year, or $77.7 per hour.

Truck Driver Owner Operator - 6mo EXP Required - OTR - $220k per year - Decker

Decker

South Point, OH

$220K/yr

Full-time

Posted 15 days ago

Job description

Looking for Owner Operators to Partner with Decker Truck Line.

Owner Operator Advantages - Partner with Decker Truck Line

Join a 90+ year, family-owned carrier that values long-term partnerships, consistent freight, and transparent pay.


Earnings & Pay
  • Earn up to $220,000 annually
  • 60% – 72% of linehaul based on experience level
  • 90% – 100% of fuel surcharge
  • Weekly settlements with clear, straightforward statements 


Freight & Settlements
  • 100% no-touch freight
  • Flatbed Operation's Require Tarping & Securing Loads
  • Consistent, reliable freight from long-standing customers
  • Choose your preferred regions, freight type, and home time


Flexibility & Control
  • You control your schedule and home time
  • No forced dispatch
  • Run the lanes that work best for you and your business


Equipment Requirements
  • Tractor must be 8 years old or newer
  • Must meet Decker’s safety and appearance standards


Why Owner Operators Choose Decker
  • Family-owned carrier with over 90 years of stability
  • Driver-first culture with accessible operations and leadership
  • Strong safety support and fair, consistent policies
  • Built for long-term success — not short-term turnover


Ask about our Lease Purchase Options. 


Apply