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Local Class A Owner Operator Jobs in Milwaukee, WI

Forward Air

CDL-A Owner Operator Driver

Waukesha, WI · On-site

$4.1K - $5.2K/wk

Best-in-class miles. Solo Owner Operators average 2,500 miles per week across Forward's closed ... A dedicated Driver Support Team is available to help with any concerns that come up, giving Owner ...

Forward Air

CDL-A Owner Operator Driver

Germantown, WI · On-site

$4.1K - $5.2K/wk

Best-in-class miles. Solo Owner Operators average 2,500 miles per week across Forward's closed ... A dedicated Driver Support Team is available to help with any concerns that come up, giving Owner ...

Clark Transfer Inc

CDL A Owner Operator

Milwaukee, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy ... class live entertainment could only be found in the major cities. Clark Transfer helped to change ...

Clark Transfer Inc

CDL A Owner Operator

Milwaukee, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy ... class live entertainment could only be found in the major cities. Clark Transfer helped to change ...

Clark Transfer Inc

CDL A Owner Operator

Brookfield, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy ... class live entertainment could only be found in the major cities. Clark Transfer helped to change ...

Clark Transfer Inc

CDL A Owner Operator

Milwaukee, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy ... class live entertainment could only be found in the major cities. Clark Transfer helped to change ...

Clark Transfer Inc

CDL A Owner Operator

Brookfield, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy ... class live entertainment could only be found in the major cities. Clark Transfer helped to change ...

Clark Transfer Inc

CDL A Owner Operator

Milwaukee, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy ... class live entertainment could only be found in the major cities. Clark Transfer helped to change ...

Clark Transfer Inc

CDL A Owner Operator

Milwaukee, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy ... class live entertainment could only be found in the major cities. Clark Transfer helped to change ...

Clark Transfer Inc

CDL A Owner Operator

Milwaukee, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy ... class live entertainment could only be found in the major cities. Clark Transfer helped to change ...

Clark Transfer Inc

CDL A Owner Operator

Milwaukee, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy ... class live entertainment could only be found in the major cities. Clark Transfer helped to change ...

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Showing results 1-20

All JobsLocal Class A Owner Operator JobsLocal Class A Owner Operator Jobs in Milwaukee, WI

Local Class A Owner Operator information

See Milwaukee, WI salary details

$634

$4.3K

$7.6K

How much do local class a owner operator jobs pay per week?

As of Aug 20, 2026, the average weekly pay for local class a owner operator 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 a local Class A owner operator?

A Local Class A Owner Operator is a professional truck driver who owns and operates their own commercial vehicle (usually a tractor-trailer) and holds a Class A Commercial Driver’s License (CDL). They typically contract with transportation companies or find their own freight, focusing on local or regional routes that allow them to return home daily or frequently. As independent business owners, they are responsible for managing their business operations, vehicle maintenance, and compliance with safety regulations. This role offers more autonomy compared to company drivers but also comes with the responsibility of handling all business-related expenses and logistics.

What are the key skills and qualifications needed to thrive as a local Class A owner operator?

To excel as a Local Class A Owner Operator, you need a valid Class A Commercial Driver’s License (CDL), a clean driving record, and knowledge of DOT regulations. Familiarity with electronic logging devices (ELDs), GPS navigation systems, and basic truck maintenance tools is typically required. Strong time management, self-motivation, and customer service skills help build client relationships and ensure on-time deliveries. These competencies are vital for maintaining safety, efficiency, and business profitability in local freight operations.

What are some common challenges faced by local Class A owner operators, and how can they be managed effectively?

Local Class A Owner Operators often face challenges such as managing their own schedules, maintaining their vehicles, and ensuring consistent work through contracts or freight brokers. Balancing time on the road with administrative tasks like invoicing and compliance paperwork can also be demanding. Effectively managing these challenges involves strong organizational skills, building reliable relationships with shippers or dispatchers, and staying proactive with vehicle maintenance to avoid unexpected downtime. Many operators find that joining reputable carrier networks or leveraging load boards helps secure steady work while allowing them to maintain some independence.

What is the difference between Local Class A Owner Operator vs Local Company Driver?

AspectLocal Class A Owner OperatorLocal Company Driver
CredentialsCommercial Driver's License (CDL) Class A, permits for haulingCDL Class A, often with company-specific training
Work EnvironmentIndependent, self-managed routes, often on own equipmentEmployed by a company, assigned routes, using company trucks
Employer & Industry UsageFreight, logistics, trucking companies, independent contractingSame industries, employed directly by carriers

In summary, Local Class A Owner Operators operate their own trucks and manage their routes independently, while Local Company Drivers work for a trucking company using company-owned equipment. Both roles require a CDL Class A license and serve similar industries, but differ mainly in equipment ownership and employment structure.

What are popular job titles related to Local Class A Owner Operator jobs in Milwaukee, WI?

For Local Class A Owner Operator jobs in Milwaukee, WI, the most frequently searched job titles are:

What job categories do people searching Local Class A Owner Operator jobs in Milwaukee, WI look for?

The top searched job categories for Local Class A Owner Operator jobs in Milwaukee, WI are:

What cities near Milwaukee, WI are hiring for Local Class A Owner Operator jobs?

Cities near Milwaukee, WI with the most Local Class A Owner Operator job openings:

Local Class A Owner Operator jobs near you
Infographic showing various Local Class A Owner Operator job openings in Milwaukee, WI as of July 2026, with employment types broken down into 1% As Needed, 73% Full Time, 19% Part Time, 1% Temporary, and 6% Contract. Highlights an 94% Physical, 1% Hybrid, and 5% Remote job distribution, with an average salary of $225,202 per year, or $108.3 per hour.

CDL Class A Owner Operator

ARROW SPECIALIZED CARRIERS INC

Kenosha, WI • On-site

$50K - $100K/yr

Full-time

Medical, Dental, Vision, PTO

Posted 13 days ago

Job description

CDL Class A Regional Truck Driver & Owner Operator

Location: Regional

Schedule: Home Daily

Pay: Weekly


Join the Arrow Specialized Carriers team! We are a family-owned transportation company committed to safety, reliability, and treating our drivers with respect.

We are currently hiring dependable Company Drivers and Owner Operators for our growing regional fleet. Enjoy steady work and competitive pay while sleeping in your own bed every night.


Why Drive with Arrow?

  • Home Daily: Regional routes designed around your life.
  • Weekly Pay: Reliable, consistent compensation.
  • Second Chance Employer: We evaluate applicants individually based on qualifications, driving history, and safety regulations.


Track 1: Company Drivers

Perfect for experienced drivers or motivated new CDL graduates looking for a stable company role.

  • Experience: 2+ years of verifiable Class A CDL experience preferred.
  • New Graduates: Recent CDL grads are welcome! We provide the support and training to help you launch your career.
  • Freight & Gear: Experience with dry van, reefer, flatbed, pneumatic or bulk tankers, or manual transmissions is a plus.


Track 2: Owner Operators

Partner with a reliable, driver-focused carrier that values professionalism and safety.

  • Equipment: Must own and operate a well-maintained Class A tractor.
  • Compliance: Valid vehicle registration and insurance that meets company/DOT standards.
  • Opportunity: Consistent freight, respected partnership, and local support.


General Requirements (All Applicants)

Minimum Qualifications

  • Valid Class A Commercial Driver’s License (CDL)
  • Current DOT Medical Card
  • Ability to pass a mandatory DOT drug screening
  • Clean driving record and commitment to cargo/road safety
  • Dependable attendance and a professional attitude

Preferred Skills & Experience

  • Experience using Electronic Logging Devices (ELDs)
  • Load securement and cargo safety knowledge
  • Strong communication and customer service skills

Ready to Join the Team?

Apply today to start driving with a carrier that puts its drivers first!