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Owner Operators Jobs in Windsor, ON (NOW HIRING)

AZ Owner Operator

Windsor, ON · On-site

  • Medical

  • Dental

  • Life

New home daily and overnight trips. Apply for more details. QUALIFICATIONS * Valid AZ driver's license * One year cross-boarder tractor trailer driving experience * Clean driving record FAST Approved ...

By submitting this application, I acknowledge that most Tim Hortons ® restaurants are independently owned and operated by franchisees. In that regard, I understand that I may be applying to a Tim ...

This job posting is for a position in a restaurant owned and operated by an independent franchisee, not QDOBA Restaurant Corp. This means the independent franchisee, and not QDOBA Restaurant Corp. ...

This job posting is for a position in a restaurant owned and operated by an independent franchisee, not QDOBA Restaurant Corp. This means the independent franchisee, and not QDOBA Restaurant Corp. ...

This job posting is for a position in a restaurant owned and operated by an independent franchisee, not QDOBA Restaurant Corp. This means the independent franchisee, and not QDOBA Restaurant Corp. ...

This job posting is for a position in a restaurant owned and operated by an independent franchisee, not QDOBA Restaurant Corp. This means the independent franchisee, and not QDOBA Restaurant Corp. ...

Production Team Member

Windsor, ON

CA$17.60 - CA$19.10/hr

By submitting this application, I acknowledge that most Tim Hortons ® restaurants are independently owned and operated by franchisees. In that regard, I understand that I may be applying to a Tim ...

By submitting this application, I acknowledge that most Tim Hortons ® restaurants are independently owned and operated by franchisees. In that regard, I understand that I may be applying to a Tim ...

By submitting this application, I acknowledge that most Tim Hortons ® restaurants are independently owned and operated by franchisees. In that regard, I understand that I may be applying to a Tim ...

Must have experience with computer diagnostics and coinciding necessary repairs Wolverine Freight has been family owned and operated for over 30 years. We offer a clean and safe working environment ...

New

By submitting this application, I acknowledge that most Tim Hortons ® restaurants are independently owned and operated by franchisees. In that regard, I understand that I may be applying to a Tim ...

Assistant Manager

Windsor, ON · On-site

CA$23.10/hr

  • Medical

  • Dental

  • Life

  • PTO

Take an owner/operator mindset by addressing issues, maintaining standards, and taking ownership of store execution. * Leverage retail technology and digital tools to enhance the customer experience ...

Some opportunities may exist with our Franchise partners, which are independently owned and operated. Recipe is committed to providing a diverse, equitable and inclusive workplace. Celebrating people ...

Some opportunities may exist with our Franchise partners which are independently owned and operated. Recipe is committed to providing a diverse, equitable and inclusive workplace. Celebrating people ...

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Showing results 1-20

Owner Operators information

See Windsor, ON salary details

$408

$3.4K

$7.4K

How much do owner operators jobs pay per week?

As of Aug 16, 2026, the average weekly pay for owner operators in Windsor, ON is $3,386.40, according to ZipRecruiter salary data. Most workers in this role earn between $1,616.02 and $5,237.83 per week, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as an owner operator?

To thrive as an Owner Operator, you need strong business management skills, a commercial driver's license (CDL), and a thorough understanding of transportation regulations and logistics. Familiarity with electronic logging devices (ELDs), freight brokerage platforms, and route planning software is often necessary. Excellent time management, self-motivation, and communication skills set standout candidates apart in this competitive field. These skills and qualities are vital to efficiently manage your own business, ensure regulatory compliance, and maintain reliable client relationships.

How do owner operators find jobs?

Owner operators find jobs through load boards, freight brokers, and direct relationships with shippers or carriers. They often use industry-specific platforms, build networks, and maintain good reputation to secure consistent work, while also managing necessary licenses and insurance requirements.

What is an owner operator?

An Owner Operator is a self-employed truck driver who owns and operates their own commercial vehicle. They either haul freight for a company under a contract or run their own independent trucking business. Responsibilities include managing expenses, securing contracts, maintaining their truck, and complying with industry regulations. Being an Owner Operator provides more control over routes and schedules but also comes with financial risks and business management responsibilities.

How much do most owner operators make?

Most owner operators in the trucking industry earn between $100,000 and $200,000 annually, depending on factors such as experience, routes, and equipment. Earnings can vary widely based on load volume, fuel costs, and operational efficiency, with some owner operators making more through specialized freight or dedicated routes.

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

Owner Operators often encounter challenges such as fluctuating fuel costs, finding consistent loads, maintaining their vehicles, and keeping up with regulatory requirements. Staying organized with digital tools for load planning and maintenance scheduling can help streamline operations. Building strong relationships with freight brokers and direct shippers may increase access to steady work, while careful budgeting can assist in managing overhead expenses. Additionally, keeping up-to-date with industry regulations can ensure your business remains compliant and operates smoothly. Addressing these challenges proactively helps promote a successful and sustainable operation.

What cities near Windsor, ON are hiring for Owner Operators jobs?

Cities near Windsor, ON with the most Owner Operators job openings:

Infographic showing various Owner Operators job openings in Windsor, ON as of August 2026, with employment types broken down into 81% Full Time, 13% Part Time, 1% Temporary, and 5% Contract. Highlights an 92% Physical, 3% Hybrid, and 5% Remote job distribution, with an average salary of $176,093 per year, or $84.7 per hour.

AZ Owner Operator

Wolverine Freight System

Windsor, ON • On-site

Full-time

Medical, Dental, Life

Posted 16 days ago


Job description

New home daily and overnight trips. Apply for more details. 

QUALIFICATIONS

  • Valid AZ driver’s license
  • One year cross-boarder tractor trailer driving experience
  • Clean driving record FAST Approved

BENEFITS

  • Weekly Pay Direct Deposit
  • Paid Benefits including Health and Dental
  • Paid Life Insurance for driver and family
  • Paid Plates & Tractor Insurance Program
  • Paid Border Crossing & Designated Tolls
  • Paid WSIB
  • Paid Terminal Parking
  • Paid Safety Equipment
  • Paid and Filed: IFTA & Heavy Use Tax

TRUCK MAINTENANCE BENEFITS

  • High Quality Standards
  • We are recognized by Canada’s leading fleet insurer as being in the top 10% of Canadian fleets when it comes to safety

Wolverine Freight System
The best company you will ever drive for!

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