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Owner Operator Jobs in Madison, WI (NOW HIRING)

Schumann Printers

Bindery Machine Operator

Fall River, WI · On-site

$20 - $25/hr

Our family-owned and operated facility is ready to welcome you aboard our award-winning team of dedicated web press and bindery experts. We currently have openings in our Finishing Department for ...

Schumann Printers

Bindery Machine Operator

Fall River, WI · On-site

$20 - $25/hr

Our family-owned and operated facility is ready to welcome you aboard our award-winning team of dedicated web press and bindery experts. We currently have openings in our Finishing Department for ...

Blystone Towing & Radiator Inc

Be Seen First

Tow Truck Operator

Portage, WI · On-site

$20 - $35/hr

Excellent communication abilities Company Description We are a family owned and operated towing and repair business. We have been open since 1950. We have a fleet of 12 tow trucks, including light ...

Blystone Towing & Radiator Inc

Be Seen First

Tow Truck Operator

Portage, WI · On-site

$20 - $35/hr

Excellent communication abilities Company Description We are a family owned and operated towing and repair business. We have been open since 1950. We have a fleet of 12 tow trucks, including light ...

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Showing results 41-60

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 7, 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.
More about Owner Operator jobs
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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, and 57% Contract. Highlights an 100% In-person job distribution, with an average salary of $230,319 per year, or $110.7 per hour.

Owner-Operator Box truck OTR Non Cdl - Quick Pay, be payed every 48hrs

ATOM LOGISTICS INC

Madison, WI

$5.5K - $8.0K/wk

Full-time

Re-posted 7 days ago

Job description

NON CDL Box Truck Owner-Operator (OTR) – $5,500 - $8000 Weekly

We are seeking committed contractors to run one of the OTR routes available. 

What We Offer:

  • Weekly gross earnings: $5,500 – $8000
  • 12% company service fee with factoring included
  • Owner-operators take 88% of the gross
  • Onboarding in as little as one day
  • You may run under our MC flexible partnership
  • Fuel card program with a great discount
  • Sign-on bonus available
  • Clean DOT inspection bonus
  • General freight – mostly no-touch
  • Assistance in acquiring your own MC

Support:

  • No forced dispatch
  • No factoring fees
  • OTR freight across 48 states
  • 2-3 weeks out
  • Fuel card program with discounts
  • Sign-on bonus available
  • Clean DOT inspection bonus
  • 24/7 ELD and safety support

Requirements:

  • 24’ or 26’ box truck (model year 2013 or newer)
  • At least 6 months of verifiable OTR experience
  • Regular driver's license - Non-CDL 
  • No more than 1 moving violation in the past 2 years

Reach us today at 872-259-1406 to find out the best available work for you!