Cross-Border Opportunities for Owner Operator Truck driver – Winnipeg
We are seeking professional, safety-oriented Owner Operators with their own tractors to join a growing and inclusive fleet with our client.
As an Owner Operator (Single or Team), you’ll be running cross-border and expedited freight across Canada and the U.S., based out of Winnipeg, MB. This is a full-time opportunity offering consistent miles, strong earning potential, and a supportive, driver-focused environment.
We encourage female operators to apply and are committed to providing a safe, respectful, and equitable work environment for all drivers.
What do we offer:
- Competitive pay up to $1.55 per mile (Team – U.S.)
- Up to $1.43 per mile (Single – U.S.)
- Consistent miles (average 10,500–12,500 miles/month)
- Estimated $120,000 – $200,000 annual revenue opportunity
- No holdback pay – semi-monthly direct deposit
- Fuel subsidy program plus fuel cards and toll support
- Paid orientation
- Additional pay: picks/drops, detention, layovers
- Paid border crossings, tolls, and operational extras
- Premiums for cross-border, specialty lanes, and FAST card
- No-touch freight – driver assistance may be required at some client sites
- State-of-the-art tools (ELD / telematics systems)
- Company-paid decals, satellite installation, and driver support
What you do:
- Transport freight across Canada and the U.S.
- Complete pickups, deliveries, and required inspections safely and efficiently
- Provide accurate trip and border documentation
- Maintain communication with dispatch using ELD/telematics systems
- Follow all Hours of Service and safety regulations (Canada & U.S.)
- Handle a mix of dry vans and refrigerated freight when required
What We’re Looking For:
- Valid Class 1/AZ License with no restrictions
- Minimum 24 months of AZ tractor-trailer experience
- Minimum 6 months U.S. driving experience (for cross-border roles)
- Must be eligible to enter the U.S.
- Well-maintained tractor that meets required specifications
- Experience with reefer units considered an asset
- Comfortable using ELDs and digital communication tools
- Clean CVOR and Driver Abstract
- Clean criminal background check (DOT compliant)
- Professional, safety-focused, and reliable attitude
Equipment Requirements:
- Tractor 2016 or newer preferred
- DEF system required (no pre-emission engines)
- Maximum weight 20,500 lbs
Why Join:
- Consistent freight across North America
- Flexible lanes (single or team opportunities)
- Strong earning potential with multiple premium pay streams
- Inclusive, driver-first environment focused on safety and respect
- Opportunity for long-term partnership and steady growth
If this sounds like a fit for you, we invite you to apply today or call 905-279-9000. This position is immediately available.
Since 1951, Drake International has been a global leader in integrated human capital solutions, delivering tailored services in recruitment, assessment and upskilling, operational efficiency, healthcare, and workplace wellbeing. We partner directly with employers to offer candidates the best opportunities at no cost, with a human-centered approach.
Recruitment decisions are led by our team. We may occasionally pilot AI-supported screening tools to support efficiency, but they are not a fixed part of our selection process. All hiring decisions are made by people, and candidates will be informed if any AI tool is involved in their assessment in accordance with the Employment Standards Act.
Drake International is an equal opportunity employer committed to accessibility, inclusivity, and diversity. Accommodation is available throughout the recruitment process. If you require accommodation, please contact your Branch Representative.
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