TTSAO Instructor of the Year Award for 2024

TTSAO Instructor of the Year Award for 2024

We are thrilled to announce that Roland “Rolly” Winnan has been awarded the prestigious TTSAO 2024 Truck Driver Instructor of the Year Award, proudly sponsored by Tenstreet.

With 35 years of experience in the trucking industry, Rolly has spent the past year making an indelible mark at Transport Driver Training in Kitchener, Ontario. His dedication and commitment to training aspiring truckers have been nothing short of extraordinary.

Jeff McKay, owner of Transport Driver Training, praises Rolly’s exceptional work ethic and devotion. “Rolly is a true pillar of our training program,” McKay said. “He arrives at our yard as early as six in the morning, even on his days off, to inspect the trucks and ensure everything is in perfect order. His attention to detail and dedication are second to none.”

Rolly’s passion for helping others shines through in his approach to training. When a student faces the disappointment of failing a road test, Rolly takes it upon himself to provide extra support. “He treats every student’s success as his own,” McKay noted. “If a student doesn’t pass, Rolly is right there the next day, offering guidance and preparation for the next attempt. His unwavering support makes him feel like family to all of us.”

Beyond his contributions at the training yard, Rolly extends his generosity to the wider community. McKay shared, “After a long day with us, Rolly doesn’t stop. He heads out to help the homeless, showing the same level of care and dedication. His commitment to making a difference is truly inspirational.”

Rolly’s dedication, both to his students and the community, exemplifies the highest standards of the trucking profession. This award recognizes his tireless efforts, compassionate nature, and the profound impact he has on those around him. Congratulations to Roland Winnan, our TTSAO 2024 Truck Driver Instructor of the Year!


Membership in the Truck Training Schools Association of Ontario can be of great benefit to you, whether you provide commercial driver training, employ drivers, or are in some other segment of the transportation industry. Join our association today to become part of this team of professionals whose goal is to improve and unify truck driver training standards, resulting in highly skilled, better prepared, entry-level and re-certified commercial drivers.

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