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Dedicated Driver Jobs in Milwaukee, WI (NOW HIRING)

Quality Carriers

Class-A CDL Company Driver OTR

Racine, WI · On-site

$1.9K - $2.2K/wk

Benefits Paid Orientation and Paid On the Job Training Dedicated Driver Manager! Weekly Direct Deposit / No Hold Back! Stability You Can Count On - Over 100 Years in Business! Personal Wellness ...

Landair

CDL-A Dedicated Truck Driver

Milwaukee, WI · On-site

$1.5K - $1.6K/wk

At Landair, you're a driver, not a number, so let us show you how we're dedicated to making things "Just Right" for you. Landair is an Equal Opportunity Employer Disability/Veteran VEVRAA Federal ...

Landair

CDL-A Dedicated Truck Driver

Kenosha, WI · On-site

$1.5K - $1.6K/wk

At Landair, you're a driver, not a number, so let us show you how we're dedicated to making things "Just Right" for you. Landair is an Equal Opportunity Employer Disability/Veteran VEVRAA Federal ...

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All JobsDedicated Driver JobsDedicated Driver Jobs in Milwaukee, WI

Dedicated Driver information

See Milwaukee, WI salary details

$786

$1.6K

$1.9K

How much do dedicated driver jobs pay per week?

As of Sep 1, 2026, the average weekly pay for dedicated driver in Milwaukee, WI is $1,575.02, according to ZipRecruiter salary data. Most workers in this role earn between $1,042.31 and $1,894.23 per week, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a dedicated driver?

To thrive as a Dedicated Driver, you need a valid commercial driver's license (CDL), a strong driving record, and a thorough understanding of transportation regulations. Familiarity with GPS navigation systems, electronic logging devices (ELDs), and route optimization software is typically required. Reliability, time management, and excellent communication skills set top performers apart in this role. These skills ensure timely and safe deliveries, regulatory compliance, and positive client relationships.

What are some common challenges dedicated drivers face, and how can they be managed?

Dedicated Drivers often face challenges such as managing tight delivery schedules, adapting to changing routes, and maintaining consistent communication with dispatch teams. Staying organized and using technology, like GPS and route planning apps, can help drivers stay on track. Building good relationships with dispatchers and understanding company procedures also make it easier to resolve issues quickly and efficiently. Regular vehicle maintenance and self-care are important to ensure safety and reliability throughout their routes.

What is the difference between Dedicated Driver vs Local Driver?

AspectDedicated DriverLocal Driver
CredentialsCommercial driver's license (CDL), clean driving recordVaries; often CDL or standard license, depending on cargo
Work EnvironmentLong-haul routes, consistent schedules, often on highwaysShort-distance deliveries, urban routes, daily home time
Employer & IndustryTrucking companies, logistics firms, retail distributionLocal businesses, courier services, food delivery
Search & Comparison IntentYes, often compared for route consistency and payNo, more focused on local delivery specifics

Dedicated Drivers typically handle long-distance routes with consistent schedules and require CDL credentials, working for trucking or logistics companies. Local Drivers focus on short-distance deliveries within urban areas, often returning home daily. Both roles may require similar licenses but differ mainly in work environment and route length.

What is a dedicated truck driving job?

A dedicated truck driving job involves transporting goods for a specific company or customer on a regular route, often with consistent schedules and routes. Drivers typically operate company-owned trucks, follow company policies, and may need a commercial driver's license (CDL) and safety training. These jobs offer stability and predictable hours compared to other trucking roles.

What are popular job titles related to Dedicated Driver jobs in Milwaukee, WI?

For Dedicated Driver jobs in Milwaukee, WI, the most frequently searched job titles are:

What job categories do people searching Dedicated Driver jobs in Milwaukee, WI look for?

The top searched job categories for Dedicated Driver jobs in Milwaukee, WI are:

Dedicated Driver jobs near you
Infographic showing various Dedicated Driver job openings in Milwaukee, WI as of August 2026, with employment types broken down into 85% Full Time, 13% Part Time, and 2% Contract. Highlights an 99% In-person, and 1% Remote job distribution, with an average salary of $81,901 per year, or $39.4 per hour.

Dedicated Regional CDL A Truck Driver | Milwaukee, WI

Knight Transportation

Milwaukee, WI • On-site

$1.8K - $2.1K/day

Other

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 16 days ago

Job description

Knight Transportation Dedicated Driver Opportunity

$95k/year on average!

Equip.Type: Dedicated

Home Time: Home Bi-Weekly

Exp. Level: Experienced (6+ Months OTR)

Description:

At Knight Transportation we have one mission: Deliver More. We are committed to delivering more for our drivers. More Miles. More Pay. More Respect!

What does it mean to be part of the most profitable and fastest growing truckload carrier in the country? So much MORE.

Job Details:

Knight Transportation is looking for Class A CDL drivers for a driver unload dedicated account with 1 – 2 unloads a week. Drivers can expect regional routes with all loads out of Maquoketa, Iowa. This is one of our top paying driving jobs.

  • Daily pay rate
  • $1,825 – $2,100 average weekly pay
  • $95,000 yearly average pay
  • 12-14 days out, 2 days home
  • Mostly round trip loads, 1-2 unloads a week with stop pay
  • Driver unload using rollers

Job Benefits:

  • Medical, Dental, Vision and Prescription Benefits for Employees and Family
  • 401k Retirement Plan With Matching, Stock Purchase Plan
  • Short & long term disability offered
  • Basic and Supplemental Life Insurance and Accidental Death and Dismemberment Insurance
  • Accident insurance, Hospital Indemnity, and Critical Illness Coverage
  • Health Care & Dependent Care Flexible Spending Accounts; Health Reimbursement Account. Paid Time Off – 3 days after 90 days of service
  • Employee Assistance Program

Job Perks:

  • 27 Terminals Nationwide
  • 24/7 Roadside Support
  • Late Model Equipment
  • Rider and Pet Policy
  • All Trucks Equipped With Inverter
  • CDL School Tuition Reimbursement
  • Free Showers Through Rewards Partners

Qualifications:

  • Must be at least 21 years old and hold a valid Class A license
  • 6 months of Class A experience within the last year or 1 year of Class A experience within the last 5 years
  • No DUI within 5 years or 10 years if CDL holder at time of DUI
  • No more than 1 preventable accident in the past 2 years, no major accident within 5 years
  • No more than 2 moving violations in the past 2 years
  • Must be able to pass a DOT physical and drug tests

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