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Owner Operators Jobs in Winnipeg, MB (NOW HIRING)

Lineage Logistics

Dispatcher

Winnipeg, MB · On-site

CA$24/hr

Experience working with company drivers, owner operators and third party carriers. * High school graduation or equivalent. * Excellent customer service abilities with a natural desire to provide ...

Tim Hortons

Team Member

Winnipeg, MB

CA$16/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 ...

Tim Hortons

Team Member

Selkirk, MB

CA$16/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 ...

Tim Hortons

Baker

Selkirk, MB

CA$16.25/hr

Flexible schedule ABOUT THE COMPANY Job applicants responding to this posting may be applying to a Tim Hortons ® restaurant independently owned and operated by a franchisee and, if so, any hiring ...

Tim Hortons

Dayshift Team Member

Winnipeg, MB · On-site

ABOUT THE COMPANY We are a family owned and operated business. Our company began in 1998 with William Kent opening a Tim Hortons restaurant in Portage La Prairie, Manitoba. Over the last 25 years our ...

Tim Hortons

Team Member

Steinbach, MB · On-site

CA$15.80/hr

Flexible schedule ABOUT THE COMPANY Job applicants responding to this posting may be applying to a Tim Hortons ® restaurant independently owned and operated by a franchisee and, if so, any hiring ...

Tim Hortons

Counter Staff

Selkirk, MB

CA$16/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 ...

Tim Hortons

Baker

Winnipeg, MB · On-site

CA$16.25/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 ...

Tim Hortons

Team Member

Winnipeg, MB

CA$16/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 ...

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Showing results 1-20

All JobsOwner Operators JobsOwner Operators Jobs in Winnipeg, MB

Owner Operators information

See Winnipeg, MB salary details

$423

$3.5K

$7.7K

How much do owner operators jobs pay per week?

As of Sep 5, 2026, the average weekly pay for owner operators in Winnipeg, MB is $3,507.04, according to ZipRecruiter salary data. Most workers in this role earn between $1,673.58 and $5,424.40 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.

What are popular job titles related to Owner Operators jobs in Winnipeg, MB?

For Owner Operators jobs in Winnipeg, MB, the most frequently searched job titles are:

What job categories do people searching Owner Operators jobs in Winnipeg, MB look for?

The top searched job categories for Owner Operators jobs in Winnipeg, MB are:

Owner Operators jobs near you
Infographic showing various Owner Operators job openings in Winnipeg, MB as of August 2026, with employment types broken down into 88% Full Time, 9% Part Time, and 3% Contract. Highlights an 92% Physical, 3% Hybrid, and 5% Remote job distribution, with an average salary of $182,366 per year, or $87.7 per hour.

Class 1 - Owner Operators - Container Work - CDI (Winnipeg)

Challenger Motor Freight Inc

Winnipeg, MB • On-site

Full-time

Re-posted 23 days ago

Job description

This opportunity is be based in Winnipeg, MB. 
What you need to be successful in the role

  • CP/CN container experienced is an asset
  • Minimum 21 years of age
  • One year of verifiable commercial vehicle driving experience in North America. 
  • Clean driving record
  • Carrier profile
  • Safety Fitness Certificate 
  • Criminal record search (no offences under Criminal Code of Canada)
  • Valid Class AZ or Class 1 driver’s licence
  • Professional attitude and desire to be part of an award-winning team
Truck requirements
  • Truck cannot be older than 2010. 
  • Must have own plates (Hwy plates required - over 161km)
  • Must have own insurance
We offer 
  • Competitive rates - paid per move!  
  • Fuel Card
  • Paid Fuel Surcharge on top of the rates
  • Paid biweekly via direct deposit
  • Open door policy


From our customers to our drivers, we know that in the transportation industry, people are our driving force.
We are always challenging ourselves to build new standards of quality and performance through leadership, respect, commitment, transparency, and teamwork.
 

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