Trucking executives say fleets must balance digital innovation with people-first strategies if they want to thrive in a fast-changing industry. They emphasized during Bridging the Barriers in Mississauga, Ont., that while artificial intelligence and automation are streamlining operations, culture, training, and generational shifts cannot be ignored.

Innocon president David Kelly said his company quickly discovered the limits of going all-digital. The ready-mix supplier rolled out an online ordering platform, but more than 30% of customers still preferred phone calls.

“Some just don’t want to use digital tools,” he said, noting that forcing technology on them risked losing business. The system has proven effective for many, but “you have to look after the entire customer base,” he added at the Women’s Trucking Federation of Canada event on Sept. 16.

For TFI, bridging barriers has meant rethinking cross-training. Executive vice-president Kristen Fess said AI is being used to build standard operating procedures that accelerate onboarding and reduce reliance on senior staff for hours of in-person training.

An employee returning from maternity leave, for example, was able to step into account management by following AI-supported guides rather than shadowing a colleague.

Fess added that agility requires exposure across the business. Dispatchers, planners, and mechanics are brought into financial and operational reviews to see how their roles affect profitability. “It’s a long game,” she said, describing agility as something built through repeated exposure to new experiences.

Purolator’s director of operations, Jason Belgrave, said absenteeism and inconsistent peer-to-peer training once slowed onboarding and spread bad habits. The courier company now relies heavily on automation, using tools like smart sorting and dynamic routing to cut training times from weeks to hours. VR headsets at its Toronto hub allow new hires to experience specialized tasks virtually before stepping onto the floor.

Benefits of cross-training

“The first instinct is to see automation as a way to cut costs,” Belgrave said. “But it’s really about redeploying people into higher-value work.” He argued fleets should view automation as a way to expand what employees can do, not just reduce headcount.

Cross-training is also paying off for Innocon. The company runs three-month rotations that temporarily reduce efficiency but prepare employees to cover gaps and step into leadership roles. Kelly said the program acts as an “insurance policy” and boosts morale by showing clear paths for advancement. “You see who can rise to the occasion,” he said, adding that younger workers especially want a holistic view of the company rather than being locked into one role for years.

Panelists agreed culture and communication are just as critical as technology. Belgrave said culture is defined by what companies reward and what they refuse to tolerate. Employees in healthy cultures are more willing to stretch beyond their roles, but leaders must provide clear tools and support when introducing change. He warned that if change fails, it is often because people have not been prepared properly.

Generational differences

Generational differences also surfaced. Gary Vandenheuvel, owner of Preferred Towing in Sarnia, Ont., and president of Professional Towing Association of Ontario, said older leaders built careers around long hours and constant availability. Younger employees, he noted, value balance and will not accept the same sacrifices. “We can’t just say, ‘Do what we did.’ We have to adapt.”

He also pointed to the disappearance of shop classes in schools as a long-term challenge. Many young people no longer graduate with hands-on skills, leaving companies to train them from scratch. That makes it even more important to build supportive workplaces that feel like communities, he said.

Technology to the rescue

Vandenheuvel highlighted how unpredictability shapes his sector. Tow operators may start the day with scheduled calls but then run entirely on minute-by-minute requests once the phones ring. That reality makes dispatch systems vital to track drivers and match the right truck to each job.

Technology is already reshaping how those calls are handled. Vandenheuvel uses AI tools to polish reports, but he was surprised to learn some operators are experimenting further. At a recent tow show, a northern Ontario fleet owner told him his after-hours dispatch is now fully managed by AI.

The consensus across the panel was clear: fleets cannot rely on technology alone. Digital systems will keep improving, but the industry’s future depends on how well companies invest in their people.