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Owner Operator Independent Contractor Jobs in Milwaukee, WI

PTL Owner-Operators

CDL A Owner-Operators

Pewaukee, WI

$150K/yr

If you're ready to take control of your career and grow your business with a carrier that values independent contractors, PTL has the opportunity you've been looking for. Our Owner Operator program ...

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All JobsOwner Operator Independent Contractor JobsOwner Operator Independent Contractor Jobs in Milwaukee, WI

Owner Operator Independent Contractor information

See Milwaukee, WI salary details

$634

$4.3K

$7.6K

How much do owner operator independent contractor jobs pay per week?

As of Sep 5, 2026, the average weekly pay for owner operator independent contractor in Milwaukee, WI is $4,330.81, according to ZipRecruiter salary data. Most workers in this role earn between $2,369.23 and $6,442.31 per week, depending on experience, location, and employer.

What is an owner operator independent contractor?

An Owner Operator Independent Contractor is an individual who owns and operates their own commercial vehicle, typically a truck, and contracts with companies to transport goods. Unlike company drivers, owner operators are self-employed and manage their own business operations, including vehicle maintenance, scheduling, and securing contracts. They have the flexibility to choose their loads and clients but are also responsible for all costs associated with running their business. This role requires strong business acumen, a commercial driver's license, and a good understanding of the transportation industry.

What are the key skills and qualifications needed to thrive as an owner operator independent contractor?

To thrive as an Owner Operator Independent Contractor, you need a valid commercial driver's license (CDL), strong business management skills, and a solid understanding of freight logistics. Familiarity with electronic logging devices (ELDs), GPS navigation systems, and basic truck maintenance is crucial, along with any required state or federal certifications. Excellent time management, self-motivation, and customer service abilities help set top performers apart. These skills and qualities are essential for maintaining compliance, maximizing profitability, and ensuring reliable service in a competitive transportation industry.

What are some common challenges owner operator independent contractors face when managing their own business?

Owner Operator Independent Contractors often encounter challenges such as managing fluctuating fuel costs, maintaining and repairing their own vehicles, and ensuring compliance with changing regulations. Balancing administrative duties like bookkeeping and securing consistent loads can also be demanding. Additionally, effective time management is crucial, as downtime or inefficient scheduling can directly impact earnings. Building strong relationships with brokers and shippers helps mitigate some of these challenges and ensures a steady workflow.

What is the difference between Owner Operator Independent Contractor vs Truck Driver?

AspectOwner Operator Independent ContractorTruck Driver
CredentialsCommercial Driver's License (CDL), vehicle registrationCDL often required, no vehicle ownership needed
Work EnvironmentOwns and operates their truck, flexible routesWorks for a company, assigned routes and schedules
Employer & Industry UsageSelf-employed, contracts with carriersEmployed by a trucking company
Search & Comparison IntentHigh overlap in responsibilities, independence

In summary, Owner Operator Independent Contractors own and operate their trucks, managing their routes and schedules, while Truck Drivers typically work for a company with set routes. Both roles require a CDL, but ownership and independence distinguish the owner operator from a standard truck driver.

What are the most commonly searched types of Owner Operator jobs in Milwaukee, WI?

The most popular types of Owner Operator jobs in Milwaukee, WI are:

Owner Operator Independent Contractor jobs near you
Infographic showing various Owner Operator Independent Contractor job openings in Milwaukee, WI as of August 2026, with employment types broken down into 1% As Needed, 71% Full Time, 22% Part Time, and 6% Contract. Highlights an 87% Physical, 3% Hybrid, and 10% Remote job distribution, with an average salary of $225,202 per year, or $108.3 per hour.

CDL-A OWNER OPERATOR/INDEPENDENT CONTRACTORS

Freymiller

Milwaukee, WI

$1.81/hr

Contractor

Re-posted 19 days ago

Job description

Bring Your Truck. Run Under Freymiller Authority.

REAL Security. REAL Freight. REAL Pay.

Driver with Confidence. Partner with Freymiller.

Are you aCDL-A Owner OperatororIndependent Contractorlooking for:

  • Steady miles
  • High-paying freight
  • Weekly pay
  • And a company thatrespects your time and hustle?

AtFreymiller, we offer consistentOTR freight, industry-leadingfuel surcharge pay, and a network that supports your business like it's our own.

  • $1.81 CPM Loaded Miles
  • Percentage Pay Option Available
  • Fuel Surcharge
  • Huge Fuel Discounts (Best in the Industry)
  • Reefer Fuel Rebate
  • Strong, Consistent Miles
  • Support You Can Count On
  • Percentage Pay Option Available

You've Got Questions. We've Got Opportunities.

Apply Today and see what's possible with Freymiller!