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Auto Transport Owner Operator Jobs in Wisconsin (NOW HIRING)

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Auto Transport Owner Operator information

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$650

$4.4K

$7.8K

How much do auto transport owner operator jobs pay per week?

As of Aug 22, 2026, the average weekly pay for auto transport owner operator in Wisconsin is $4,436.79, according to ZipRecruiter salary data. Most workers in this role earn between $2,426.92 and $6,600.00 per week, depending on experience, location, and employer.

What is an auto transport owner operator?

An Auto Transport Owner Operator is a self-employed truck driver who specializes in transporting vehicles using a car hauler or similar equipment. They own or lease their truck and trailer, manage their own business operations, and secure contracts with dealerships, auctions, and private clients. Responsibilities include vehicle loading, securing, transportation, and delivery while ensuring compliance with regulations. This role offers independence and high earning potential but requires significant investment in equipment, insurance, and operational costs.

What skills and qualifications are needed to thrive as an auto transport owner operator?

To thrive as an Auto Transport Owner Operator, you need a valid commercial driver’s license (CDL), knowledge of vehicle loading and safety regulations, and experience with long-haul trucking. Familiarity with electronic logging devices (ELDs), load boards, and GPS routing systems is typically required, along with proper insurance and authority from the Department of Transportation. Strong organizational skills, customer service abilities, and attention to detail are valuable soft skills for managing schedules, contracts, and client relationships. These skills ensure safe, efficient vehicle transport, compliance with regulations, and a reputation for reliability in a competitive industry.

What are common challenges auto transport owner operators face in their daily work?

Auto Transport Owner Operators often deal with complex logistics, including planning efficient routes, managing delivery timelines, and handling unexpected issues like traffic delays or vehicle breakdowns. Balancing regulatory compliance, such as hours-of-service rules and safety standards, while maintaining good customer service can also be demanding. Additionally, operators must manage their business operations, including billing, insurance, and vehicle maintenance. Staying organized and proactive helps minimize disruptions and supports smooth, profitable operations.

How to become an auto transport owner operator?

To become an auto transport owner operator, you typically need a valid commercial driver's license (CDL), a reliable truck or trailer, and proper insurance coverage. Many operators start by gaining experience as company drivers, then establish their own authority with the Federal Motor Carrier Safety Administration (FMCSA) and obtain necessary permits. Strong driving skills, knowledge of routes, and business management are essential for success in this role.

What are popular job titles related to Auto Transport Owner Operator jobs in Wisconsin?

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What job categories do people searching Auto Transport Owner Operator jobs in Wisconsin look for?

The top searched job categories for Auto Transport Owner Operator jobs in Wisconsin are:

Auto Transport Owner Operator jobs near you
Infographic showing various Auto Transport Owner Operator job openings in Wisconsin as of August 2026, with employment types broken down into 49% Full Time, 49% Part Time, 1% Contract, and 1% Nights. Highlights an 99% Physical, and 1% Remote job distribution, with an average salary of $230,713 per year, or $110.9 per hour.

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

Diamond Transportation

Green Bay, WI

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