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Contract Driver Jobs in Madison, WI (NOW HIRING)

Lead contract lifecycle activities from review through execution and ongoing management ... Valid driver's license and acceptable driving record required. Why Join MyPath? At MyPath, you'll ...

CDL Driver

Madison, WI ยท On-site

Commercial Driver's License (CDL A or CDL B) with Air Brakes Endorsement Current DOT Medical ... contract of service covering the engagement.

CDL Driver

Madison, WI ยท On-site

$23.51 - $29.90/hr

... contract of service covering the engagement. Benefits * Competitive salaries for all team members paid weekly * 401(k) Retirement Plan with company matching * Employee Stock Purchase Program * Paid ...

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Showing results 1-20

Contract Driver information

See Madison, WI salary details

$11

$37

$86

How much do contract driver jobs pay per hour?

As of Aug 22, 2026, the average hourly pay for contract driver in Madison, WI is $37.26, according to ZipRecruiter salary data. Most workers in this role earn between $17.45 and $63.22 per hour, depending on experience, location, and employer.

What is a contract driver?

Contract drivers are independent professionals who transport goods, packages, or passengers for companies or individuals based on a contractual agreement rather than as direct employees. They may work for delivery services, ride-share platforms, or logistics companies, often using their own vehicles. Contract drivers are responsible for managing their schedules, maintaining their vehicles, and handling taxes as independent contractors. This role offers flexibility but does not typically include benefits like health insurance or paid time off.

What does a contract driver do?

As a contract driver, your primary responsibilities are to drive a vehicle to transport materials or items on a contract basis. Your duties vary depending on the details of each contract. You may drive a truck on a set delivery route to transport cargo, or you may have independent courier contracts and pick up and deliver materials for businesses, medical service providers, or private individuals. If you work as a courier, you may coordinate with a dispatch operator to receive information for each delivery. Contract drivers typically own the vehicle that they drive.

What skills and qualifications are needed to thrive as a contract driver?

To thrive as a Contract Driver, you need a valid driver's license, a clean driving record, and familiarity with local routes and traffic laws. Experience with GPS navigation systems, delivery management apps, and, in some cases, a commercial driver's license (CDL) are typically required. Strong time management, reliability, and customer service skills make someone stand out in this role. These skills and qualities ensure timely, safe deliveries and positive client interactions, which are critical for building trust and repeat business.

What are common challenges contract drivers face and how can they be managed?

Contract drivers often face challenges such as unpredictable schedules, variable workloads, and maintaining their own vehicles. Managing these challenges involves strong time-management skills, staying organized with route planning, and ensuring regular vehicle maintenance. Many contract drivers also join professional networks or use mobile apps to streamline their work and find new opportunities, which can help reduce downtime and increase efficiency.

What is the difference between Contract Driver vs Delivery Driver?

AspectContract DriverDelivery Driver
CredentialsDriver's license, possibly commercial licenseDriver's license, sometimes specialized for certain vehicles
Work EnvironmentIndependent or contracted, often flexible hoursEmployed by a company, regular routes, scheduled hours
Employer & Industry UsageFreelance or contracted basis across various industriesCompany-employed, retail, food, or parcel delivery sectors
Search & Comparison IntentHigh overlap in credentials and work environmentSimilar roles but typically more structured employment

Contract drivers operate independently or on a contractual basis, offering flexibility and often working across multiple industries. Delivery drivers are usually employed by companies, following scheduled routes. Both roles require a valid driver's license, but contract drivers tend to have more autonomy, while delivery drivers have more structured hours.

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

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

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

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

Infographic showing various Contract 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 $77,498 per year, or $37.3 per hour.

Contract Specialist

Mypath

Madison, WI โ€ข On-site, Remote

Full-time

Posted 17 days ago


Job description

Majority Women Employee-Owned. Empowered by Everyone to Transform Lives.


Overview

At MyPath Support Services, we believe that strong partnerships create better outcomes for the individuals we serve. We're looking for an organized, collaborative, and detail-oriented Contract Specialist to help manage the full lifecycle of funder contracts across 3 of our organizations.

This position is open to candidates who reside in Wisconsin or Indiana. The role is primarily remote, with occasional in-office meetings, events, and travel to MyPath locations as needed.

In this role, you'll work closely with leaders across Finance, Operations, Admissions, and Executive Leadership to ensure funder contracts are reviewed, negotiated, maintained, and compliant with funding and regulatory requirements. If you enjoy problem-solving, building relationships, and managing complex projects, we'd love to hear from you.

What You'll Do

As our Contract Specialist, you will:

  • Lead contract lifecycle activities from review through execution and ongoing management.

  • Coordinate the review process across multiple MyPath operating companies.

  • Draft, review, edit, and organize a variety of contract documents.

  • Support contract negotiations with internal stakeholders and external funding partners.

  • Serve as a primary liaison with funding agencies by managing rate requests, communications, and documentation.

  • Monitor contracts for compliance with licensing requirements, governmental regulations, and organizational standards.

  • Identify potential contract risks and recommend solutions.

  • Partner with Finance, Operations, Admissions, and Executive Leadership to resolve contract-related issues.

  • Assist with credentialing, contract audits, and other funder requirements.

  • Research state policies and legislative changes that may impact contracts and funding.

  • Maintain confidentiality while managing sensitive information and business agreements.

What We're Looking For

Qualifications

  • Bachelor's degree preferred.

    • Associate's degree with relevant professional experience may be considered.

  • Exceptional organizational skills and attention to detail.

  • Strong written and verbal communication skills.

  • Ability to manage multiple priorities while meeting deadlines.

  • Comfortable learning and utilizing multiple technology platforms and online funder portals.

  • Ability to work collaboratively across departments and build strong working relationships.

Preferred Qualifications

  • 1-2 years of experience in healthcare, human services, managed care, residential services, or a related field.

  • Experience with contract administration or contract management.

  • Project management experience is a plus.

Work Environment

  • This position is primarily remote, with occasional in-office meetings or events a few times each year. For candidates who prefer working from an office, office workspace can be arranged.

  • Fast-paced, collaborative environment.

  • Occasional travel to MyPath locations as needed.

  • Valid driver's license and acceptable driving record required.

Why Join MyPath?

At MyPath, you'll join a mission-driven organization committed to helping people live their best lives. We offer opportunities to collaborate with talented professionals, contribute to meaningful work, and grow your career in an organization that values integrity, innovation, and teamwork.

If you're passionate about organization, collaboration, and making an impact behind the scenes, we'd love to have you on our team. Apply today and help support the partnerships that make our mission possible.

Additional Information

MyPath and its Operating Companies provide specialized services and dignified care for children, adolescents and adults with special needs. Our companies provide a spectrum of services and support which promote the ability of those we serve to live as independently as possible in the community.


MyPath is composed of a beautifully diverse spectrum of employees with different characteristics, abilities, and life experiences. We believe that equitable, diverse, and inclusive practices in our workspaces are integral to the existence of MyPath. We value our diverse spectrum of Owners, the individuals we serve and the communities we encounter.


Our success as an organization is directly proportional to our ability to create belonging and genuinely engage our Owners and potential Owners. We ask for demographic information so that we can be intentional in supporting our Owners best. Although not required, we would appreciate you sharing to help our commitment of cultivating a diverse, equitable, inclusive, and belonging MyPath.


Our Culture

At MyPath, we support an ownership culture throughout the organization. Our culture is based on our five beliefs and behaviors:

  • Passion

  • Accountability

  • Teamwork

  • Openness

  • Continuous Learning and Innovation

As an employee owner, you can expect transparency, respect and appreciation. You'll impact the place you work and map a career within MyPath. With your passion and our breadth of services, your options are nearly limitless!

MyPath is proudly Majority Women Employee-Owned, with women leading at every level from the frontline to the boardroom. Our strength comes from all of us. Every Owner, regardless of gender, plays a vital role in shaping our culture, driving our mission, and building a workplace where opportunity and ownership are shared by all.

MyPath is an Equal Opportunity Employer (EOE) committed to fostering a diverse, equitable, and inclusive workplace. We embrace the unique characteristics, abilities, and life experiences of our employees and believe that equitable and inclusive practices are essential to our success. We value the diversity of our Owners, the individuals we serve, and the communities we engage with.