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Contract Delivery Driver Jobs in Madison, WI (NOW HIRING)

Zimbrick Automotive

Sales Consultant Used

Madison, WI · On-site

... sales contracts, deliver vehicles and follow-up regularly to ensure customer satisfaction ... A valid driver's license and good driving record Must be 18 years or older Equal Opportunity ...

Southern Shingles

CDL Driver

Madison, WI · On-site

The CDL Driver at SRS ensures safety, timely delivery of building materials to job sites, verifies ... contract of service covering the engagement.

SRS Building Products - Madison

CDL Driver

Madison, WI · On-site

$23.51 - $29.90/hr

The CDL Driver at SRS ensures safety, timely delivery of building materials to job sites, verifies ... service without a fully executed contract of service covering the engagement. Benefits

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Showing results 21-40

All JobsContract Delivery Driver JobsContract Delivery Driver Jobs in Madison, WI

Contract Delivery Driver information

See Madison, WI salary details

$8

$18

$25

How much do contract delivery driver jobs pay per hour?

As of Sep 5, 2026, the average hourly pay for contract delivery driver in Madison, WI is $18.60, according to ZipRecruiter salary data. Most workers in this role earn between $16.25 and $20.34 per hour, depending on experience, location, and employer.

What is a contract delivery driver?

Contract delivery drivers are independent workers who are hired by companies or individuals to deliver goods, packages, or food on a contractual basis rather than as full-time employees. They typically use their own vehicles and set their own schedules, working for one or multiple delivery platforms such as Amazon Flex, DoorDash, or local courier services. Contract delivery drivers are responsible for picking up items from specified locations and ensuring timely, accurate delivery to customers. They are considered independent contractors, which means they handle their own taxes, insurance, and expenses related to their work.

How does being a contract delivery driver differ from a full-time delivery position in terms of schedule flexibility and daily workflow?

As a contract delivery driver, you'll typically enjoy greater control over your schedule, allowing you to select shifts or delivery blocks that suit your availability. Unlike full-time employees, contract drivers are generally responsible for planning their own routes, managing time efficiently, and handling customer interactions independently. This flexibility can be appealing, but it also means you'll need strong self-motivation and organizational skills to meet deadlines and service expectations. Additionally, contract drivers are often responsible for their own vehicle maintenance and expenses, which is an important consideration.

What are the key skills and qualifications needed to thrive as a contract delivery driver, and why are they important?

To thrive as a Contract Delivery Driver, you need a valid driver’s license, good driving record, knowledge of local routes, and often a high school diploma or equivalent. Familiarity with GPS navigation systems, route optimization apps, and sometimes package scanning devices is typically required. Reliability, strong time management, and effective customer service skills set top performers apart in this role. These abilities ensure timely, accurate deliveries and positive customer experiences, which are crucial for client satisfaction and repeat business.

What is the difference between Contract Delivery Driver vs Full-Time Delivery Driver?

AspectContract Delivery DriverFull-Time Delivery Driver
CredentialsDriver's license, clean driving recordDriver's license, clean driving record
Work EnvironmentIndependent, flexible schedule, often on a per-job basisCompany-owned vehicles, fixed schedule, regular hours
Employer & Industry UsageFreelance or third-party logistics companiesRetail, food delivery, courier companies
Search & Comparison IntentOften compared for flexibility and independenceCompared for stability and benefits

The main difference between a Contract Delivery Driver and a Full-Time Delivery Driver lies in employment status, schedule flexibility, and benefits. Contract drivers typically work independently with flexible hours, while full-time drivers are employed by a company with fixed schedules and benefits. Your choice depends on your preference for independence versus stability.

What are the most commonly searched types of Delivery Driver jobs in Madison, WI?

The most popular types of Delivery Driver jobs in Madison, WI are:

What are popular job titles related to Contract Delivery Driver jobs in Madison, WI?

For Contract Delivery Driver jobs in Madison, WI, the most frequently searched job titles are:

What job categories do people searching Contract Delivery Driver jobs in Madison, WI look for?

The top searched job categories for Contract Delivery Driver jobs in Madison, WI are:

What cities near Madison, WI are hiring for Contract Delivery Driver jobs?

Cities near Madison, WI with the most Contract Delivery Driver job openings:

Contract Delivery Driver jobs near you
Infographic showing various Contract Delivery Driver job openings in Madison, WI as of August 2026, with employment types broken down into 1% As Needed, 67% Full Time, 28% Part Time, and 4% Contract. Highlights an 98% Physical, and 2% Remote job distribution, with an average salary of $38,676 per year, or $18.6 per hour.

CDL A Midwest Regional Truck Driver

Fremont Contract Carriers

Jefferson, WI

$80K - $90K/yr

Full-time

Retirement, PTO

Posted 3 days ago

New

Job description

Now hiring CDL-A company truck drivers for Midwest regional runs with weekly home time!

Midwest Regional CDL-A Truck Driver Jobs Feature:

  • Must have 18+ months of verifiable experience within the last 3 years.
  • Earn $80,000-$90,000 per year
  • $85,150 avg. earnings per year
  • 2,500 to 3,000 miles per week delivering in: NE, IA, IL, IN, MN, KS, WI, MO, OH
  • 70% drop and hooks; all driver no touch freight
  • Option to go home every weekend for 34 to 48 hrs.
  • Full benefits package with a 401(k) program
  • FREE Sirius XM for all company drivers!
  • $0.06 quarterly safety bonus
  • Paid vacation after a year
  • All equipment is newer and have APUs, refrigerator/freezers, 2000-watt inverters and much more!
  • Rider program after 90 days
  • Driver referral bonus program

CDL-A Truck Driver Job Requirements:

  • Class A CDL
  • 18+ months of verifiable experience required within the last 3 years
  • Must meet all Federal Motor Carrier Safety Regulations
  • No serious traffic violations in the past 3 years
  • No more than 4 jobs in the past 3 years
Get started with Fremont Contract Carriers, one of the country’s BEST FLEETS! APPLY NOW!

Fremont Contract Carriers is a special career destination for Class A truck drivers looking for a better regional driving opportunity! When you’re named among the top 20 Best Fleets to Drive For (16 out of the last 18 years!) and overall BEST FLEET winner 3 times, it means you know how to treat CDL-A truck drivers right while offering stable careers and steady support.

Right now, FCC is hiring CDL-A truck drivers for our Midwest Regional fleet running no touch, mostly drop and hook freight between Nebraska and Ohio. Stay off the coasts and earn more with an award-winning company – Fremont Contract Carriers!

Apply