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Owner Operator Transport Jobs in Wisconsin (NOW HIRING)

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Owner Operator Transport information

See Wisconsin salary details

$650

$4.4K

$7.8K

How much do owner operator transport jobs pay per week?

As of Sep 3, 2026, the average weekly pay for owner operator transport 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 owner operator transport?

Owner Operator Transport jobs are positions where individuals own and operate their own commercial vehicles, such as trucks or vans, to transport goods for clients or companies. Unlike company drivers, owner operators are responsible for maintaining their vehicles, managing their business expenses, and often finding their own clients or contracts. This role offers greater independence and potentially higher earnings, but also comes with more responsibilities, such as handling insurance, taxes, and compliance with transportation regulations. Owner operators can work independently or lease their services to larger freight companies.

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

To thrive as an Owner Operator Transport, you need a valid commercial driver's license (CDL), strong knowledge of transportation regulations, and experience in logistics and vehicle maintenance. Familiarity with electronic logging devices (ELDs), GPS navigation systems, and basic accounting or fleet management software is essential. Strong business acumen, time management, and customer service skills help set successful owner operators apart. These competencies are crucial for ensuring safe, efficient deliveries, maintaining compliance, and running a profitable independent transport business.

What are common challenges owner operator transport professionals face when managing their own business?

Owner Operator Transport professionals often encounter challenges such as fluctuating fuel prices, securing consistent contracts, and maintaining their vehicles to avoid costly downtime. Additionally, balancing time between driving, administrative tasks, and compliance with regulations can be demanding. Building solid relationships with clients and brokers is crucial for steady work, and adapting to changing industry requirements helps ensure long-term success.

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

AspectOwner Operator TransportTruck Driver
CredentialsCommercial Driver's License (CDL), business registrationCommercial Driver's License (CDL)
Work EnvironmentOperates own truck, manages businessWorks for an employer, company-owned trucks
Employer/Industry UsageSelf-employed or independent contractor in freight industryEmployed by a trucking company or fleet
Search/Comparison IntentLooking for independent freight operatorsSeeking employment as a company driver

Owner Operator Transport involves individuals who own and operate their own trucks, managing their business and freight loads. Truck Drivers typically work for a company, driving company-owned trucks. The main difference lies in ownership, business responsibilities, and employment status, with Owner Operators having more independence but also more responsibilities.

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

For Owner Operator Transport jobs in Wisconsin, the most frequently searched job titles are:

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

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

Owner Operator Transport jobs near you
Infographic showing various Owner Operator Transport 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.

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

Diamond Transportation

Howard, WI

Contractor

Re-posted 17 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