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Local Dedicated Owner Operator Jobs in Milwaukee, WI

Forward Air

CDL-A Owner Operator Driver

Waukesha, WI · On-site

$4.1K - $5.2K/wk

A dedicated Driver Support Team is available to help with any concerns that come up, giving Owner Operators the backing they need to run a successful business. Owner Operator Perks & Support

Forward Air

CDL-A Owner Operator Driver

Germantown, WI · On-site

$4.1K - $5.2K/wk

A dedicated Driver Support Team is available to help with any concerns that come up, giving Owner Operators the backing they need to run a successful business. Owner Operator Perks & Support

RidenRoll

Taxi Owner-Operators

Milwaukee, WI · On-site

We are dedicated to delivering top-notch services, fostering a competitive market, and ensuring a ... Local state license plate. What We Offer: * Access to state-of-the-art technology and tools.

RidenRoll

Taxi Owner-Operators

Milwaukee, WI · On-site

We are dedicated to delivering top-notch services, fostering a competitive market, and ensuring a ... Local state license plate. What We Offer: * Access to state-of-the-art technology and tools.

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Showing results 21-40

All JobsLocal Dedicated Owner Operator JobsLocal Dedicated Owner Operator Jobs in Milwaukee, WI

Local Dedicated Owner Operator information

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

To thrive as a Local Dedicated Owner Operator, you need a valid commercial driver’s license (CDL), a clean driving record, business acumen, and experience with local freight routes. Familiarity with electronic logging devices (ELDs), route planning software, and basic truck maintenance tools is typically required. Strong organizational skills, self-motivation, and excellent customer service abilities set top performers apart. These skills and qualities are crucial for ensuring timely deliveries, operational efficiency, and sustained business success in a competitive transportation market.

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

Local Dedicated Owner Operators often face challenges such as maintaining consistent routes, managing vehicle maintenance, and balancing work-life commitments due to tight delivery schedules. Building strong relationships with dispatchers and shippers can help secure regular loads and minimize downtime. Additionally, staying proactive with vehicle upkeep and leveraging route planning technology can reduce unexpected delays and expenses, while clear communication with clients and family can support work-life balance.

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

AspectLocal Dedicated Owner OperatorLocal Company Driver
CredentialsCommercial Driver's License (CDL), experience in hauling specific freightCDL, basic driving experience
Work EnvironmentOperate own truck, flexible schedules, independent workDrive company-owned trucks, structured schedules
Employer & Industry UsageFreight carriers, logistics companies, owner-operated fleetsCarriers, logistics firms, large transportation companies

In summary, Local Dedicated Owner Operators own and operate their trucks, offering flexibility and independence, while Local Company Drivers work for a company using their trucks with more structured schedules. Both roles require a CDL and are common in local freight hauling, but differ mainly in ownership and work setup.

What is a local dedicated owner operator?

A Local Dedicated Owner Operator is a self-employed truck driver who owns and operates their own commercial vehicle, and contracts with a specific company to transport goods within a designated local area. Unlike over-the-road drivers, local dedicated operators typically work regular routes and are home daily or nightly. They benefit from consistent schedules and steady work, but are also responsible for their truck’s maintenance, insurance, and other business expenses. This role combines the independence of being an owner-operator with the stability of dedicated routes.

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

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

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

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

Local Dedicated Owner Operator jobs near you
Infographic showing various Local Dedicated Owner Operator job openings in Milwaukee, WI as of August 2026, with employment types broken down into 1% As Needed, 75% Full Time, 22% Part Time, and 2% Contract. Highlights an 90% Physical, 1% Hybrid, and 9% Remote job distribution.

Sprinter Van/Cargo Van Owner Operator

Offmax Logistics LLC

Oak Creek, WI • Remote

$2.0K - $4.5K/wk

Full-time

Re-posted 3 days ago

Job description

About the Job:
HIRING  TSA DRIVERS
Off Max Logistics LLC is a driver-oriented company that seeks out the most effective ways to help drivers in the transportation industry. We understand what it's like to be on the road, and that is why we hold drivers in such high regard because we know how important they are to the economy. We are looking for owner-operators  who are Sprinter van / Cargo van TSA DRIVERS and who are highly motivated. We offer high-paying loads daily based on your needs and you do not have to be exclusive to us alone.
QUALIFICATION:
  • Note driver must have a TWIC card or STA certificate and must be ready to pass the TSA test

BENEFITS/PAY:
  • (Quick pay option available ) being paid 24 hours after dropping off the load
  • Pay is from $1,000.00 - $3000.00 per week (depending on miles and location)
  • Create your own flexible schedule.
  • You choose where you want to run local, regional, or OTR loads.
  • No forced dispatch.
  • No hidden fees.
  • Weekly pay – Direct deposit.
  • Support 24/7 with an industry-qualified staff.
  • Dedicated dispatch and operation manager for every driver.

MINIMUM QUALIFICATIONS:
  • Own a Sprinter Van or Cargo Van under 10,000 lbs. in GVWR. (14ft and below). NO RENTALS OR LEASED.
  • Valid U.S. driver's license.
  • A clean driving record will be a big plus.
  • Meet all legal qualifications required to carry out the work including a background check.
  • At least 21 years old.
  • Can speak, read, and write in English.
  • Insurance policy (must).
  • Decent and Safe Work History.
  • TWIC CARD IS A MUST-HAVE. We can sponsor your TSA certification.

Equipment Requirements:
  • Cargo Van/Sprinter Van.
  • Vehicle from 2010 onward.
  • Clean cargo space.
  • No decals.
  • Good equipment condition.

Job Type:
  • Full-time.
  • Part-time.
  • Contract.
  • Temporary.

Off Max Logistics LLC is currently expanding our team of owner-operators and fleet owners to meet the rising demand of our customers.
WE'RE HIRING FROM ALL STATES.
HR  email: hrteam@offmaxlogisticsllc.com
Main Line: (888 )900-5874
Contact HR press 1
We are a driver-oriented company
Off Max Logistics LLC is a driver-oriented company that seeks out the most effective ways to help drivers in the transportation industry. We understand what it's like to be on the road, which is why we hold drivers in such high regard because we know how important they are to the economy. We are a growing company and always searching for highly motivated individuals ready to innovate and create a better industry.
We are a driver-oriented company.