Owner/Operator Recruitment and Retention Specialist

Why Work for Canada Cartage
Canada Cartage is one of Canada’s leading transportation and logistics providers with over 100 years of experience supporting businesses nationwide. Through our national network of terminals and distribution centres, we deliver dedicated fleet, freight, and supply chain solutions to many of Canada’s leading brands. We are proud to be recognized as a Top Fleet Employer by Trucking HR Canada, an Employer of Distinction, and one of Forbes Canada’s Best Employers.
Career Opportunity
Owner/Operator Driver Recruiter & Retention Specialist
Position Summary
Reporting to the Director of Talent Acquisition, the Owner/Operator Driver Recruiter & Retention Specialist plays a key role in supporting Canada Cartage's growth by attracting, hiring, and retaining qualified owner-operators and drivers across the transportation sector. This position builds strong relationships with candidates, Operations leaders, brokers, and internal partners while providing clear guidance on compensation, requirements, and expectations.
Location: Mississauga, Ontario
Schedule: Monday to Friday, day shift
Work Arrangement: On-site position
What You Will Do

• Manage full-cycle recruitment for owner-operators and drivers across the business.
• Source, screen, assess, and engage candidates to ensure alignment with role requirements, safety standards, and company expectations.
• Partner closely with hiring managers, Operations leadership, Talent Acquisition, brokers, and other internal stakeholders to understand hiring needs and priorities.
• Build and maintain strong candidate pipelines and long-term relationships with owner-operators and drivers.
• Explain owner-operator and driver compensation packages, including rates, deductions, incentives, fuel surcharges, operating expenses, and overall earnings.
• Identify and help resolve compensation or contract discrepancies, responding to questions clearly and professionally.
• Lead direct and sometimes challenging conversations, manage expectations, hold stakeholders accountable, and escalate concerns when appropriate.
• Track and report on key recruitment and retention metrics, including time to fill, quality of hire, and turnover.
• Contribute ideas to improve recruitment processes, candidate experience, retention, and overall effectiveness.
• Support colleagues and contribute to broader team priorities as required.

What You'll Bring

• 3+ years of experience in driver recruitment, owner-operator recruitment, or a related transportation role such as dispatch or professional AZ driving.
• Experience working with owner-operators, brokers, and AZ drivers.
• Knowledge of CVOR requirements, Driver Qualification Files, commercial vehicle compliance, insurance requirements, driver abstracts, and related records.
• Strong understanding of owner-operator and driver pay structures, contracts, rates, deductions, incentives, fuel surcharges, operating expenses, and earnings calculations.
• Experience using applicant tracking systems and recruitment tools is an asset.
• Strong written and verbal communication skills in English; French language skills are an asset.

Key Qualities and Expectations

• Maturity and professionalism: Demonstrates sound judgment, emotional intelligence, and the ability to handle sensitive or difficult situations calmly and professionally.
• Strong communication: Comfortable having direct and sometimes challenging conversations with owner-operators, brokers, and Operations leadership. Able to push back respectfully, manage expectations, and hold people accountable.
• Independence and accountability: A self-starter who takes ownership, makes informed decisions, solves problems, and does not require constant direction or follow-up.
• Positive and solutions-oriented approach: Remains professional under pressure and contributes positively to the team environment.
• Collaboration: Works effectively with Operations, Talent Acquisition, and other internal stakeholders, while supporting colleagues beyond immediate responsibilities when needed.
• Confidence and resilience: Does not shy away from conflict, difficult personalities, or challenging conversations. Knows when to stand firm and when to escalate.
• Organization and urgency: Manages competing priorities effectively in a fast-paced, high-volume environment while maintaining accuracy and follow-through.
• On-site commitment: Comfortable working five days per week in the Mississauga office.

Why People Love Working at Canada Cartage
Canada Cartage offers a supportive, team-oriented workplace built on collaboration and respect, with opportunities for career growth and development. Employees benefit from recognition programs that celebrate performance and teamwork, company perks including discounts on hotels, entertainment, gym memberships, and more, as well as team events such as summer barbeques and driver appreciation week. As a well-established organization, Canada Cartage provides the stability of a company that continues to grow while remaining committed to supporting the communities where we operate.
Accessibility Commitment
Canada Cartage is committed to meeting the accessibility needs of persons with disabilities in accordance with the Accessible Canada Act (ACA). Accommodation is available throughout the recruitment process and employment upon request.
Application Process
We thank all applicants for their interest; however, only those selected for an interview will be contacted. Canada Cartage is an equal opportunity employer, and successful candidates may be required to complete pre-employment verifications in accordance with company policies.