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Owner Operators Jobs in Windsor, ON (NOW HIRING)

East Side Mario's

Guest Service Server

Windsor, ON · On-site

CA$17.60/hr

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 ...

East Side Mario's

Day Host

Windsor, ON · On-site

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 ...

Leamington - JK Home Services

Painter

Chatham, ON · On-site

... closely with operator, this is the right job for you!!! Benefits: The position is open to ... business directly through the owner and make weekly bonuses! Including- * Full-time hours

Tim Hortons

Assistant Manager

Kingsville, ON · On-site

Through your knowledge of the quick service industry you take pride in supporting the Owner in the ... well as follow all operating guidelines for each piece of equipment * Assist in recruiting ...

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Showing results 21-40

All JobsOwner Operators JobsOwner Operators Jobs in Windsor, ON

Owner Operators information

See Windsor, ON salary details

$408

$3.4K

$7.4K

How much do owner operators jobs pay per week?

As of Sep 3, 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 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.

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.

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.

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 online platforms, industry networks, and maintain good communication to secure consistent work, while also managing necessary licenses and insurance requirements.

How much do most owner operators make?

Most owner operators earn between $100,000 and $200,000 annually, depending on factors such as experience, routes, and load types. Earnings can vary widely based on fuel costs, maintenance, and operational efficiency, with successful operators often managing their own schedules and equipment to maximize profit.

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For Owner Operators jobs in Windsor, ON, the most frequently searched job titles are:

What job categories do people searching Owner Operators jobs in Windsor, ON look for?

The top searched job categories for Owner Operators jobs in Windsor, ON are:

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

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

Owner Operators jobs near you
Infographic showing various Owner Operators job openings in Windsor, ON as of August 2026, with employment types broken down into 88% Full Time, 9% Part Time, and 3% Contract. Highlights an 93% Physical, 2% Hybrid, and 5% Remote job distribution, with an average salary of $176,093 per year, or $84.7 per hour.

Retail Merchandising Reps

Merchandising Consultants Associates

Chatham, ON • On-site

$18 - $22/hr

Contractor

This job post has expired today. Applications are no longer accepted.

Job description

Merchandising Consultants Associates

Department: Store Transformations
Title: Retail Merchandising Team Lead & Team Members
Location: Travel to Windsor, ON
Job Type: Full-Time Temporary Contract

MCA is a proudly Canadian owned and operated leader in retail merchandising and in-store execution. We partner with Canada and the USA's top brands, delivering exceptional service that blends agility, experience, and a people-first mindset. Our mission is to provide executional excellence and agile in-store support, so brands thrive where it matters most, on the shelf and in the hands of consumers.

We are looking for experienced Retail Merchandising Team Leads and Merchandisers for a 1-week intensive store transformation project at a major big-box retailer in Windsor, ON from 24 to 28 August 2026.

Wage: $18 - $22 per hour + weekly completion bonus
Hours: 40 hours per week
Schedule: Daytime between 7:00am and 4:30pm
Benefits: Travel Pay, hotel accommodation + per diems available

What You'll Do

As part of the Store Transformations team, you will work under on-site leadership to deliver precise, efficient execution, including:

  • Resetting categories to planogram standards
  • Building endcaps and promotional displays
  • Installing new pricing, signage, and labels
  • Moving, assembling, and placing small store fixtures
  • Maintaining safety, cleanliness, and execution standards throughout the project
What You'll Bring

We are seeking reliable, safety-conscious individuals who can perform consistently in a fast-paced retail environment. Additionally, candidates should be organized and maintain a professional and calm demeanor.

  • Prior experience working on store resets or transformations
  • Minimum 2 years of hands-on merchandising and planogram experience.
  • Proven experience executing planograms in a retail or big box environment.
  • Ability to follow detailed instructions with precision.
  • Strong attention to detail and time management skills.
  • Adaptable, calm, and professional under pressure.
  • Physically capable of lifting up to 40lbs, and performing continuous standing, bending, reaching, and lifting for long periods.
  • Has steel-toed safety footwear
APPLY NOW!

We are currently hiring for this role.
Applicants must reside in the specified location and be legally eligible to work in Canada.
MCA is an equal opportunity employer and provides accommodations throughout the hiring process.
Apply now and join a people-first team committed to meaningful work and measurable impact.

Employment Type: CONTRACTOR

Apply