Driver Trainer

Midland Transport is seeking an experienced and results-driven Driver Trainer to support the assessment, onboarding, and development of professional drivers across linehaul, transport pick-up and delivery (P&D), and courier operations. This role ensures all new drivers meet company safety, compliance, and performance standards through road evaluations, drug testing coordination, and structured onboarding programs. The Driver Trainer role is based in Brampton, Ontario and reports to our Manager, Driver Development & Training.

Benefits To Joining Midland: 

•    A dynamic, safe, and rewarding work environment

•    A flexible health, drug, dental, and vision plan

•    RRSP matching program

•    Employee & Family Assistance Programs

•    Health & Wellness reimbursements, includes gym memberships, fitness classes or online workout programs

•    3 weeks' paid vacation

•    Maternity leave top-up program

•    Growth and progression opportunities within Midland Transport and large network of the JD Irving group of companies

Driver Assessment & Qualifications:

• Conduct comprehensive road tests for Class 1, Class 3 and Class 5 driver candidates across linehaul, transport, P&D, and courier operations


• Evaluate driver competency in vehicle handling, defensive driving, safety compliance, and operational procedures


• Coordinate and/or administer pre-employment drug and alcohol testing in accordance with company policy and regulator requirements in Canada and the United States


• Provided clear pass/fail recommendations and detailed assessment feedback to Talent Acquisition and Operations


• Other duties as assigned

Onboarding & Orientation:

• Lead new driver orientation sessions, ensuring consistent delivery of company policies, safety standards, and operational expectations


• Facilitate onboarding programs that reinforce company values, safe driving behaviours, and service standards


• Ensure all required documentation, certifications, and compliance requirements are completed prior to dispatch

Coaching & Development:

• Provide on-road and in-classroom coaching to drivers to improve safety, performance, and efficiency


• Reinforce best practices in customer service, compliance, and vehicle handling


• Conduct structured 30-60-90-day check-ins with newly hired drivers


• Identify early performance or engagement concerns and escalate as appropriate


• Support driver integration into the organization and promote long-term retention

Partnerships with Talent Acquisition

• Collaborate closely with the Talent Acquisition team to support hiring needs and candidate pipelines


• Support recruitment initiatives, including job fairs, hiring events, and driver outreach as needed

• Minimum of 5 years experience as a professional driver (Class 1 preferred) in a fast-paced transportation business


• Demonstrated safe driving record and strong knowledge of transportation regulations


• Experience in driver training, coaching and/or mentoring is strongly preferred


• Strong understanding of linehaul, transport, P&D and/or courier operations


• Knowledge of hours of service, safety compliance, and industry best practices essential


• Excellent observational and evaluation capabilities


• Clear professional communication skills (verbal and written)


• Sound judgment and decision-making, particularly in safety-related matters


• Ability to build relationships across Operations, Safety and HR

Working Conditions

• Combination of classroom, yard, and on-road environments


• Regular travel between terminals may be required


• Flexible schedule to support hiring and operational needs.