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Owner Operator Jobs in Winnipeg, MB (NOW HIRING)

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

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

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

Baker

Winnipeg, MB

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

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 ...

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Showing results 1-20

All JobsOwner Operator JobsOwner Operator Jobs in Winnipeg, MB

Owner Operator information

See Winnipeg, MB salary details

$324

$3K

$7.9K

How much do owner operator jobs pay per week?

As of Sep 7, 2026, the average weekly pay for owner operator in Winnipeg, MB is $3,023.10, according to ZipRecruiter salary data. Most workers in this role earn between $817.10 and $4,961.71 per week, depending on experience, location, and employer.

What is an owner operator?

Owner operators are independent truck drivers or small business owners who own and operate their own commercial vehicles. They either lease their services to larger freight carriers or contract directly with clients to transport goods. Unlike company drivers, owner operators are responsible for managing their own business expenses, such as fuel, maintenance, insurance, and taxes. This role offers more autonomy and the potential for higher earnings, but it also comes with greater financial risk and responsibility.

What does an owner operator do?

The term Owner-Operator refers to a trucking professional who owns their truck and drives it as an independent contractor. Many companies hire independent operators to haul goods for them. Using contractors allows construction companies to keep pace with the rise and fall of demand for their products without the overhead cost of maintaining a fleet of vehicles that may be insufficient in one season and excessive in another. Owner-Operators need to hold a Commercial Driver's License (CDL) in the class that allows them to drive their vehicle and have sufficient training in operating and maintaining the machine. They can choose their own schedule and pick which jobs to take.

What are the key skills and qualifications needed to thrive as an owner operator, and why are they important?

To thrive as an Owner Operator, you need a valid commercial driver's license (CDL), strong knowledge of transportation regulations, and experience in truck driving and logistics. Familiarity with fleet management software, GPS navigation systems, and compliance tools like electronic logging devices (ELDs) is essential. Excellent time management, business acumen, and customer service skills help set top performers apart in this role. These skills and qualities are crucial for ensuring safe, efficient operations and building a successful, profitable transportation business.

What are common challenges owner operators face when managing their own trucking business?

Owner Operators often encounter challenges such as maintaining cash flow, managing fluctuating fuel costs, and ensuring their vehicles are properly maintained to avoid unexpected downtime. Balancing administrative tasks—like scheduling, invoicing, and compliance—with time on the road can also be demanding. Building relationships with reliable clients or brokers and navigating complex regulations are crucial for long-term success. Staying organized and proactive in handling these responsibilities helps Owner Operators thrive in a competitive industry.

What is the difference between Owner Operator vs Truck Driver?

AspectOwner OperatorTruck Driver
CredentialsCommercial Driver's License (CDL), business registrationCDL, basic driving license
Work EnvironmentOwn truck, self-managed scheduleCompany-owned trucks, set schedules
EmployerSelf-employed or independent contractorEmployers or carriers
Work FlexibilityHigh, controls own routes and hoursLimited, dictated by employer

Owner Operators own and operate their trucks, managing their own schedules and business. Truck Drivers typically work for a company, following set routes and schedules. The main difference lies in independence and business ownership, with Owner Operators having more control but also more responsibilities.

More about Owner Operator jobs

What are the most commonly searched types of Owner Operator jobs in Winnipeg, MB?

The most popular types of Owner Operator jobs in Winnipeg, MB are:

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

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

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

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

Owner Operator jobs near you
Infographic showing various Owner Operator job openings in Winnipeg, MB as of August 2026, with employment types broken down into 46% Full Time, 52% Part Time, 1% Contract, and 1% Nights. Highlights an 97% Physical, 1% Hybrid, and 2% Remote job distribution, with an average salary of $157,201 per year, or $75.6 per hour.

Cross-Border Owner-Operator Team

Bison Transport

Winnipeg, MB • On-site

Full-time

Re-posted 1 hour ago

Job description

$3000 Sign on Bonus. Earn up to $36.4K/month. Get Paid On Time. Every Time. This open-board, Canada/U.S. long-haul position requires you to be on the road 5 to 7 days at a time averaging 20K miles per month.

  • Southbound freight could depart into any of the lower 48 states
  • Northbound freight could go into any of the Canadian Provinces and Territories
  • Required to drive on Highway 17 in Ontario 12 months of the year
  • Required to drive U.S. Mountains 12 months of the year
  • Assigned unit requires 24 days on the road per month
  • Regional freight might be required
  • Must be able to lift 50 lbs. or more
  • Must be able to haul all commodities

Candidate Profile:

  • Owner-Operator team with 24 months tractor-trailer experience
  • Must have a qualified team partner
  • Tractor must be equipped with a DEF system
  • Valid Class 1/AZ License is required
  • Must be eligible to drive in the U.S.
  • Reliable, flexible, and punctual
  • Strong communication skills
  • Values safety


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