From Behind the Wheel to Human Resources: How Jason Lerato is Transforming Trucking Culture

published on 16 May 2025

The trucking industry is often portrayed through stereotypes of long, lonely highways and gruff personalities. But for Jason Lerato, a seasoned HR manager and driver services leader based in Winnipeg, Canada, it's about something much deeper – the human connections that keep the wheels turning.

"Truckers are a lonely bunch," Lerato explains in a recent State of Work Today podcast. "They don't want to phone their dispatcher and talk about marital problems or kid problems. But if you're the kind of HR that is approachable and real, they'll approach you."

This human-centered approach forms the foundation of Lerato's philosophy: in an industry dominated by highways and schedules, success comes from understanding the personal journeys of those behind the wheel. His unique career path from long-haul driver to HR leader has positioned him to bridge critical gaps in an industry facing significant transformation.

From Driver's Seat to HR Office: A Journey of Understanding

Before becoming an HR professional, Lerato spent nearly two decades behind the wheel. "I sat behind the wheel off and on I would say close to 20 years," he shares. "You name the province, you name the state, city - I've been there." This extensive road experience gives him invaluable insight into the challenges drivers face.

When Lerato reached a crossroads in his career, tired of life on the highway, he approached management with an ultimatum: "Either I'm quitting the company or teach me the other side of the business." His employers recognized his value and moved him to dispatch. Though dispatching wasn't his passion, this transition eventually led him to discover his true calling in HR and driver services.

The difference between dispatch and HR was striking to Lerato. While dispatchers primarily coordinate logistics, HR professionals have the opportunity to connect with drivers on a deeper level. "In the office as HR, I had drivers spill their guts and tears flowing down their eyes and just talking about real life," he recounts. "I get what they're going through. I get what it's like to have a relationship break, your kids not want to talk to you when you're on the road for so long."

This empathy has become Lerato's superpower in an industry where understanding the human element is often overlooked.

Navigating Industry Transformation and Demographics

The Canadian trucking industry is undergoing significant demographic shifts. Unlike the common perception of an aging workforce, Lerato has observed a surge of younger drivers, predominantly from South Asia.

"I would say probably 80, 90% of those that come across my desk and I interview actually come from the South Asian area of the world, predominantly East Indian, and I would say a majority are in their 20s and 30s," Lerato notes. These younger drivers view trucking as a respected career path and bring strong technical aptitude to an increasingly digital industry.

This demographic shift has required adaptation in recruitment strategies. Lerato embraced social media platforms like TikTok and Instagram to reach this younger, tech-savvy audience. "I had to adjust in order to see them come to my desk and fill a truck and start a new career," he explains.

The influx of young, educated immigrants has been vital for the industry's sustainability. "If we relied on just those born and raised in Canada, generation after generation, the trucking industry in Canada is done," Lerato states plainly. This reality underscores the importance of inclusive HR practices that welcome and support diverse workforces.

Building Culture in a Mobile Workforce

One of the most significant challenges in trucking HR is cultivating a strong corporate culture when your workforce is scattered across thousands of miles. Lerato approaches this challenge with a philosophy centered on regular, meaningful contact.

"Stay involved in that driver's life," he advises. "Whether some people don't like phone calls, so let's WhatsApp them, let's text them... how are you doing? You keeping it above water? Talk to me."

For Lerato, showing genuine interest in drivers' lives builds the trust necessary for a healthy workplace culture. He takes time to learn about cultural celebrations important to his diverse workforce, posting social media acknowledgments of holidays like Diwali and supporting drivers who need extended time off to visit family in their home countries.

This approach paid dividends when he hired five drivers from India who had left their previous employer due to payment issues. By investing in regular communication and showing interest in their personal lives, Lerato built relationships that extended beyond the workplace. Even after they moved to another part of Canada for immigration reasons, they maintained connections with him.

Three Key Insights from Lerato's HR Approach

1. Authenticity Over Everything

The trucking industry has its share of empty promises and disappointments. Lerato's counter-approach is refreshingly straightforward: "Be honest, be real. People can see through BS," he states. "That has helped me with everything in life."

Drawing from his own experiences of being misled as a driver, Lerato prioritizes transparency in recruitment and management. "Too many times I've been lied to as a driver. I get sold this beautiful song and dance. Two months in, I realized hardly any of it was true."

His honesty extends to acknowledging both strengths and weaknesses of his employers. By setting realistic expectations from the start, he builds the foundation for trust with drivers who may have been burned by false promises in the past.

2. Adding Value Through Personal Connection

When asked about his philosophy for building workplace culture, Lerato references wisdom from his wife: "Where can I add value?" This question guides his interactions with everyone from drivers to mechanics to dispatchers.

"Where can I add value to my drivers in their life, in their career, to my dispatcher across my glass window, to that mechanic who is having a really bad day because something happened in the weekend," he explains.

This value-focused mindset extends beyond office hours. "My phone went off in the evening, even though I didn't really have to answer that phone," Lerato shares. "Maybe their dispatcher's ignoring them and they're on the side of the road and that's dangerous."

His commitment to adding value manifests in practical ways, such as advocating for better pay for drivers and creating a culture where safety truly comes first. "When they come to a company that actually not only gives lip service to 'hey, we care about you,' but follows up with checks and 'are you okay?' That makes a massive difference in the industry."

3. Prioritizing People Over Profits

In an industry where cost-cutting measures like "Drivers Inc." or corporation pay models are widespread (Lerato estimates they're used by over 50% of companies in Manitoba), his people-first approach stands out.

He takes time to educate new drivers about the risks of these payment models, which may initially seem attractive but can lead to tax troubles down the road. "Corporation pay sounds really attractive, but Revenue Canada or CRA will knock on your door one day," he warns recruits.

This commitment to people extends to safety practices. While electronic logs have improved industry safety, Lerato recognizes they create pressure for drivers to "chase the clock." His message to drivers is unequivocal: "If you're tired, and I mean, you're just bagged, park... You'll never get in trouble, at least not with the company I was with. I'd rather them come home than find them in a ditch somewhere."

This ethos saves lives. Lerato shares a story of a driver whose health emergency was discovered because the company actively monitored drivers' wellbeing. "We ended up calling the Ontario Provincial Police and doing a safety check. And sure enough, he had a very serious health issue and could have died in the truck... letting the drivers know that I care more about you than what's on the back of that trailer."

Embracing Technology While Maintaining the Human Touch

Looking ahead, Lerato sees technology, particularly AI, playing an increasing role in trucking HR. He's embraced tools like ChatGPT to enhance policy development, address compliance issues, and navigate complex HR situations like harassment claims.

"ChatGPT has been incredible in helping form the answer," he explains. While not relying 100% on AI recommendations, he values how these tools help direct his thinking and prepare him for conversations with legal specialists.

His approach to technology mirrors his broader philosophy: use the tools available to better serve people. Whether it's social media for targeted recruitment or AI for policy development, technology is valuable when it enhances human connections rather than replacing them.

The Road Ahead

As the trucking industry faces challenges from demographic shifts to trade tensions between Canada and the US, Lerato's blend of operational experience and human-centered leadership offers a compelling model for HR professionals.

His journey from behind the wheel to behind the desk has given him a unique perspective that bridges divisions within the industry. By prioritizing authentic communication, cultural understanding, and genuine care for individuals, he demonstrates how HR can transform workplace culture even in highly distributed, mobile workforces.

For those looking to connect with Jason Lerato or learn more about his approach to trucking HR, he can be reached through LinkedIn

In an industry focused on moving goods, Lerato reminds us that it's the people who truly matter. As he puts it, "I care more about you than what's on the back of that trailer." It's this philosophy that has defined his career and continues to shape his impact on the trucking industry.

Listen to the entire podcast here.

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