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
At Midland, we’re not just moving freight — we’re building the next generation of transportation. We’ve been one of the most trusted carriers in Canada and the United States for over 55 years. We are driven by superior quality service, innovation, and a commitment to excellence. We’re investing in technology to deliver measurable customer-focused solutions, and we’re also committed to sustainability and growth.
Joining Midland means becoming part of a dynamic company that values safety, continuous improvement, and results. Our employees are the driving force behind our success, and we’re proud to foster a workplace where talent thrives, ideas are valued, and careers are built for the long haul. Whether on the road or in a service centre or office, every Midland employee helps build lasting relationships with our customers. We’re looking for motivated and skilled people who want to contribute to our high-performing team and be part of a business that is growing, evolving, and setting the standard in transportation and logistics.
Let’s drive success together.
Founded in 1882, J.D. Irving, Limited (JDI) has operations in Canada and the United States and are a team of 20,000 dedicated employees. At J.D. Irving, Limited, you are part of a dynamic team of professionals who lead with integrity and are passionate about delivering results. With a culture that nurtures talent and creates an inclusive workplace, you can grow your career across our various operating divisions.
We are committed to creating accessible environments for our colleagues, candidates, and customers. Requests for accommodation due to a disability (which may be visible or invisible, temporary, or permanent) can be made at any stage of application and employment. We encourage candidates to make their accommodation needs known so that we can provide equitable opportunities.
Worried you do not meet all the requirements? Studies have shown that many applicants apply only to job opportunities when they feel they meet 100% of the criteria. We promote an inclusive environment where everyone is appreciated, recognized, and empowered to contribute fully. If you are interested in this position but are worried you did not meet all the requirements, we would encourage you to still apply.
We appreciate your interest in our company however only those candidates selected for an interview will be contacted.
