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Transportation Owner Operator Jobs in Florida (NOW HIRING)

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Transportation Owner Operator information

See Florida salary details

$481

$3.3K

$5.7K

How much do transportation owner operator jobs pay per week?

As of Sep 9, 2026, the average weekly pay for transportation owner operator in Florida is $3,284.87, according to ZipRecruiter salary data. Most workers in this role earn between $1,796.15 and $4,886.54 per week, depending on experience, location, and employer.

What is a transportation owner operator?

A Transportation Owner Operator is an individual or business that owns and operates their own commercial vehicle, such as a truck or van, to transport goods or freight for clients or companies. Unlike company drivers, owner operators are independent contractors who manage their own business operations, including vehicle maintenance, insurance, and finding contracts. They often work with freight brokers or logistics companies to secure hauling jobs. Transportation Owner Operators have the flexibility to choose their routes and schedules but also bear the costs and responsibilities of running their own business.

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

To thrive as a Transportation Owner Operator, you need a valid commercial driver’s license (CDL), a strong knowledge of logistics, and solid experience in freight hauling or trucking. Familiarity with fleet management software, GPS navigation, and compliance with Department of Transportation (DOT) regulations is essential. Outstanding time management, self-motivation, and customer service skills set top performers apart in this role. These skills and tools are critical for ensuring safe, efficient, and profitable operations in a highly competitive transportation industry.

What are some common challenges transportation owner operators face in managing their own business?

Transportation Owner Operators often encounter challenges such as fluctuating fuel prices, securing consistent freight, and managing vehicle maintenance costs. Balancing time on the road with administrative tasks, like invoicing and compliance with transportation regulations, is also essential. Building relationships with brokers and shippers can help ensure a steady workflow, while staying organized and proactive about truck upkeep can reduce unexpected downtime. Adapting to changing industry regulations and maintaining a strong safety record are key to long-term success.

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

AspectTransportation Owner OperatorTruck Driver
CredentialsCommercial Driver's License (CDL), vehicle insuranceCDL often required, no ownership needed
Work EnvironmentOperate own or leased trucks, flexible routesDrive company-owned trucks, fixed routes
Employer & IndustryIndependent or contracted, freight/logistics industryEmployers or carriers, transportation industry

Transportation Owner Operators own or lease their trucks and operate independently, often managing their own schedules. Truck Drivers typically work for a company, driving company-owned trucks on assigned routes. Both roles require a CDL and are integral to freight transportation, but Owner Operators have more control and responsibility over their equipment and business operations.

What cities in Florida are hiring for Transportation Owner Operator jobs?

Cities in Florida with the most Transportation Owner Operator job openings:

Transportation Owner Operator jobs near you
Infographic showing various Transportation Owner Operator job openings in Florida as of August 2026, with employment types broken down into 1% As Needed, 63% Full Time, 34% Part Time, and 2% Contract. Highlights an 98% Physical, 1% Hybrid, and 1% Remote job distribution, with an average salary of $170,813 per year, or $82.1 per hour.

Truck Driver Owner Operator - 2yrs EXP Required - OTR - Diamond Transportation

Daytona Beach, FL

Diamond Transportation
Trucking • 11 - 50 employees
Learn more about Diamond Transportationexternal

Full-time

Re-posted 24 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