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Owner Operator Jobs in Wisconsin (NOW HIRING)

Beyondfreightinc

Owner Operator

Menomonee Falls, WI

$8K - $12K/wk

GOLD STANDARD TRANSPORT Tinley Park, IL Owner Operator CDL A Truck Driver - Dry Van - 1099 Independent Contractor (Remote) Experienced Owner Operators wanted! Run as a 1099 Independent Contractor ...

Beyondfreightinc

Owner Operator

Sheboygan, WI

$8K - $12K/wk

GOLD STANDARD TRANSPORT Tinley Park, IL Owner Operator CDL A Truck Driver - Dry Van - 1099 Independent Contractor (Remote) Experienced Owner Operators wanted! Run as a 1099 Independent Contractor ...

Beyondfreightinc

Owner Operator

De Pere, WI

$8K - $12K/wk

GOLD STANDARD TRANSPORT Tinley Park, IL Owner Operator CDL A Truck Driver - Dry Van - 1099 Independent Contractor (Remote) Experienced Owner Operators wanted! Run as a 1099 Independent Contractor ...

Beyondfreightinc

Owner Operator

Appleton, WI

$8K - $12K/wk

GOLD STANDARD TRANSPORT Tinley Park, IL Owner Operator CDL A Truck Driver - Dry Van - 1099 Independent Contractor (Remote) Experienced Owner Operators wanted! Run as a 1099 Independent Contractor ...

Beyondfreightinc

Owner Operator

Kenosha, WI

$8K - $12K/wk

GOLD STANDARD TRANSPORT Tinley Park, IL Owner Operator CDL A Truck Driver - Dry Van - 1099 Independent Contractor (Remote) Experienced Owner Operators wanted! Run as a 1099 Independent Contractor ...

OnWay Transport

Truck Owner Operator

Madison, WI · On-site

$550/day

OnWay Transport is in search of a reliable Owner Operator with a 26' Box Truck with a lift gate. Driver will be picking up medical supplies in Madison, WI, delivering to Chicago, IL and back to ...

OnWay Transport

Truck Owner Operator

Madison, WI · On-site

$550/day

OnWay Transport is in search of a reliable Owner Operator with a 26' Box Truck with a lift gate. Driver will be picking up medical supplies in Madison, WI, delivering to Chicago, IL and back to ...

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Showing results 1-20

All JobsOwner Operator JobsOwner Operator Jobs in Wisconsin

Owner Operator information

See Wisconsin salary details

$650

$4.4K

$7.8K

How much do owner operator jobs pay per week?

As of Jun 12, 2026, the average weekly pay for 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 Does an Owner-Operator Do?

The term Owner-Operator refers to a trucking professional who owns their truck and drives it as an independent contractor. Many companies hire independent operators to haul goods for them. Using contractors allows construction companies to keep pace with the rise and fall of demand for their products without the overhead cost of maintaining a fleet of vehicles that may be insufficient in one season and excessive in another. Owner-Operators need to hold a Commercial Driver's License (CDL) in the class that allows them to drive their vehicle and have sufficient training in operating and maintaining the machine. They can choose their own schedule and pick which jobs to take.

What are the key skills and qualifications needed to thrive as an Owner Operator, and why are they important?

To thrive as an Owner Operator, you need a valid commercial driver's license (CDL), strong knowledge of transportation regulations, and experience in truck driving and logistics. Familiarity with fleet management software, GPS navigation systems, and compliance tools like electronic logging devices (ELDs) is essential. Excellent time management, business acumen, and customer service skills help set top performers apart in this role. These skills and qualities are crucial for ensuring safe, efficient operations and building a successful, profitable transportation business.

What company in Texas is paying truckers $14000 a week?

Owner operators in trucking can potentially earn $14,000 a week through high-paying freight contracts, efficient route management, and fuel savings. Such earnings are typically associated with experienced drivers working with large carriers or specialized loads, often requiring strong driving skills and proper licensing. However, actual weekly income varies based on factors like load type, mileage, and operational costs.

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 earning more through specialized freight or dedicated contracts.

What are Owner Operators?

Owner operators are independent truck drivers or small business owners who own and operate their own commercial vehicles. They either lease their services to larger freight carriers or contract directly with clients to transport goods. Unlike company drivers, owner operators are responsible for managing their own business expenses, such as fuel, maintenance, insurance, and taxes. This role offers more autonomy and the potential for higher earnings, but it also comes with greater financial risk and responsibility.

What is the difference between Owner Operator vs Truck Driver?

AspectOwner OperatorTruck Driver
CredentialsCommercial Driver's License (CDL), business registrationCDL, basic driving license
Work EnvironmentOwn truck, self-managed scheduleCompany-owned trucks, set schedules
EmployerSelf-employed or independent contractorEmployers or carriers
Work FlexibilityHigh, controls own routes and hoursLimited, dictated by employer

Owner Operators own and operate their trucks, managing their own schedules and business. Truck Drivers typically work for a company, following set routes and schedules. The main difference lies in independence and business ownership, with Owner Operators having more control but also more responsibilities.

Why do most people quit trucking?

Many owner operators quit trucking due to long hours, high operating costs, and inconsistent income. The demanding schedule, maintenance responsibilities, and regulatory compliance can also contribute to job dissatisfaction and burnout.

Is there a $7500 tax credit for truck drivers?

There is no specific $7,500 tax credit exclusively for truck drivers. However, owner operators and commercial drivers may qualify for various tax deductions related to vehicle expenses, equipment, and business costs, which can reduce taxable income. It's advisable to consult a tax professional for personalized guidance on available credits and deductions based on your specific situation.

What are some common challenges Owner Operators face when managing their own trucking business?

Owner Operators often encounter challenges such as maintaining cash flow, managing fluctuating fuel costs, and ensuring their vehicles are properly maintained to avoid unexpected downtime. Balancing administrative tasks—like scheduling, invoicing, and compliance—with time on the road can also be demanding. Building relationships with reliable clients or brokers and navigating complex regulations are crucial for long-term success. Staying organized and proactive in handling these responsibilities helps Owner Operators thrive in a competitive industry.
More about Owner Operator jobs
What are the most commonly searched types of Owner Operator jobs in Wisconsin? The most popular types of Owner Operator jobs in Wisconsin are:
What are popular job titles related to Owner Operator jobs in Wisconsin? For Owner Operator jobs in Wisconsin, the most frequently searched job titles are:
What job categories do people searching Owner Operator jobs in Wisconsin look for? The top searched job categories for Owner Operator jobs in Wisconsin are:
What cities in Wisconsin are hiring for Owner Operator jobs? Cities in Wisconsin with the most Owner Operator job openings:
What are popular job titles related to Owner Operator jobs in WI? For Owner Operator jobs in WI, the most frequently searched job titles are:
Owner Operator jobs near you

Owner Operator

Beyondfreightinc

Menomonee Falls, WI

$8K - $12K/wk

Full-time, Contractor

Posted 13 days ago

Job description

GOLD STANDARD TRANSPORT Tinley Park, IL

Owner Operator CDL A Truck Driver – Dry Van – 1099 Independent Contractor (Remote)

Experienced Owner Operators wanted! Run as a 1099 Independent Contractor with high earnings, no forced dispatch, and freedom across all 48 states.
Recruiting Department contact:
630-998-8588
464-249-0494

Earnings Potential:
  • Average weekly paycheck: $8,000 – $12,000
  • $2.20 – $2.50 per mile gross
  • Keep 88% of the gross
  • Dry van average ≈ $2.30/mile | Reefer loads higher (≈ $3.00/mile) – reefers welcome
What We Offer:
  • Fuel discounts $0.35/gallon + Pilot/Flying J cards
  • Weekly paychecks
  • 24/7 dispatch & ELD support
  • 20+ load boards + no black-listed brokers
  • Experienced dispatch team (9+ years)
  • After-hours 24/7 support
  • Rate confirmations sent directly to you
  • We pay for your fuel to Chicago, IL if you rent a trailer from us
Equipment & Costs:
  • Trailer rental: $250/week (includes physical damage insurance)
  • Cargo & liability insurance: $300/week (dry van) / $350/week (reefer)
  • ELD support: $65/week
  • Optional occupational insurance: $150/month
  • Escrow (no own trailer): $1,500
Safety Bonuses:
  • Clean Level 3: $250
  • Clean Level 2: $500
  • Clean Level 1: $750
Requirements:
  • Valid CDL Class A license
  • Own tractor in good condition
  • Minimum 2 years OTR experience preferred
  • Clean/acceptable MVR & background
  • Willing to work as 1099 Independent Contractor

If you're a professional Owner Operator looking for strong pay and real freedom, apply now!

Job Type: Full-time / Independent Contractor (1099)
Work Location: Remote (OTR – All 48 States)