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Owner Operator Jobs in Madison, WI (NOW HIRING)

ALFA FREIGHT INC

Box Truck Owner Operator OTR

Madison, WI · On-site

$5.5K - $8.0K/wk

NON CDL Box Truck Owner-Operator (OTR) - $5,500 - $8,000 Weekly We are seeking committed contractors to run one of the OTR routes available What We Offer: * Weekly gross earnings: $5,500 - $8,000 ...

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All JobsOwner Operator JobsOwner Operator Jobs in Madison, WI

Owner Operator information

See Madison, WI salary details

$649

$4.4K

$7.7K

How much do owner operator jobs pay per week?

As of Aug 14, 2026, the average weekly pay for owner operator in Madison, WI is $4,429.21, according to ZipRecruiter salary data. Most workers in this role earn between $2,423.08 and $6,588.46 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.

Are owner operators making money?

Owner operators can make a profit depending on factors such as freight rates, operating costs, and efficiency. Successful owner operators typically manage expenses like fuel, maintenance, and insurance while securing consistent loads and maintaining good driving records. Earnings vary widely based on experience, routes, and market conditions.

What is an owner operator?

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.

What are 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.
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Owner Operator jobs near you
Infographic showing various Owner Operator job openings in Madison, WI as of August 2026, with employment types broken down into 43% Full Time, 55% Part Time, 1% Contract, and 1% Nights. Highlights an 99% Physical, and 1% Remote job distribution, with an average salary of $230,319 per year, or $110.7 per hour.

9-15 Ft Freight Cargo/Sprinter Van DOT Owner-Operators

Fox Carriers

Monona, WI • On-site

Contractor

Re-posted 15 days ago

Job description

9–15 Ft Freight Cargo / Sprinter Van DOT Owner-Operators Needed
Fox Carriers is looking for reliable Owner-Operators with Cargo or Sprinter Vans (DOT) for stable full-time or part-time cooperation.
If you own a cargo or sprinter van and want access to quality loads, consistent support, and competitive rates — join our team.
Requirements:
  • Must be 23 years old or older.
  • Clean background and motor vehicle record for the past 5 years.
  • No rental vehicles.
  • Vehicle year must be 2011 or newer.
  • 9–15 ft cargo space required.
  • Straps, E-Tracks, and PPE required.
  • Punctuality, flexibility, and responsibility.

What We Offer:
  • 24/7 dispatcher support
  • No forced dispatch
  • No touch freight
  • Layover, detention, and TONU paid
  • Full-time and part-time opportunities
  • Contract-based work

Our experienced dispatchers are trained to secure the best loads available on the market and help maximize your weekly earnings.
Additional advantage:
TWIC card or Hazmat endorsement gives access to more load opportunities and higher earning potential.
Join our team and get the stability, support, and rates you deserve.
Fox Carriers logo

About Fox Carriers

Sourced by ZipRecruiter

Fox Carriers is an experienced Professional Logistics Company. We have expanded and opened a direction with a database of 7 Car Hauler trucks. We offer a wide range of car delivery solutions. Provide you with Accurate and Competitive shipping prices for one of our machines. Timing and Attention to detail are in our DNA so we treat every shipment with special care.Our goal is to make the delivery process simple and smooth, no matter how many bumps in the road.

Industry

Transportation and warehousing

Company size

11 - 50 Employees

Headquarters location

Stamford, CT, US

Social media

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