Some careers start with a plan. Others begin in the pit lane. For Oleg Cytowicz, it was the latter: A race weekend steered him straight into a lifelong journey in fleet management.

In the latest Fleet Legends episode, sponsored by Legend Fleet, we sat down with Cytowicz to talk about his start, his lessons, and his advice for the next generation of fleet professionals. His story proves what many of us already know: while technology and telematics keep fleets moving, it’s the people who keep them thriving.

From Pit Crew to Fleet Desk

Cytowicz’s fleet career began with a little luck and a lot of curiosity.

“I was a casual employee at Lever Brothers,” he recalled. “One of the directors noticed my strange work schedule (I was always off Fridays and Mondays). I told him I was part of a race team pit crew and needed travel time. He said, ‘Well, we’ve got an opening in fleet, and you’re a car guy. How about I put your name in the hat?’”

That moment changed everything. He landed a role as a clerk under the late Frank Klaus, another name many consider a fleet legend.

“When I started, we tracked everything by hand,” Cytowicz said with a laugh. “Expense reports, mileage, replacement cycles, all on paper. We were just about at the turning point of when the abacus was introduced.”

From Ledgers to Laptops

If anyone has seen firsthand how technology reshaped fleet, it’s Cytowicz.

“The speed of technological development is incredible,” he said. “When I brought in my own college computer with Lotus 1-2-3, it changed everything. Suddenly, we could calculate projections instantly instead of flipping through ledgers.”

That early push toward automation foreshadowed decades of transformation. Today, he sees technology as both a blessing and a challenge.

“Now, mileage, expenses, and reports are all automated through FMC systems and telematics,” Cytowicz said. “It’s amazing how far we’ve come, but it’s also a lot of data. Fleet managers have to stay focused so they don’t get lost in it.”

People First, Always

Despite the tech talk, Cytowicz returns to a simple truth: fleet management starts and ends with people.

“As a fleet manager, you’re the hub of the wheel,” he explained. “You touch every department (finance, HR, procurement, operations) and you impact every driver. Get to know the people you work with. Learn what challenges they face. Understand how your decisions affect their day.”

He stressed the importance of communication and empathy. “If you make a change to policy or vehicles, it’s not just a spreadsheet adjustment. It affects someone’s daily routine. You have to understand both sides of that,” he added.

Building a Strong Fleet Process

When asked about rookie mistakes, Cytowicz didn’t hesitate to turn them into opportunities.

“Mistakes are learning experiences,” he said. “But don’t rely on others to think for you. If you’re handed a report or a recommendation, ask how they got to that conclusion. Be inquisitive. Understand the process, not just the output.”

That curiosity extends to his approach with emerging tools like AI.

“AI is only as good as the person who programmed it,” he said. “It’s you who has to present that data. If your boss asks how you got it, that bot isn’t going to be sitting next to you explaining the math.”

His advice came with a memorable lesson from a friend: “If AI cuts a 30-minute task down to five, use the other 25 minutes to review and understand the results. It’s still 30 minutes well spent.”

Communication in Leadership is Key

Cytowicz learned early that presenting information effectively is as important as collecting it.

“When rolling out a policy or a change, tailor your message,” he said. “Executives want bullet points and impact. Your implementation team needs clarity and collaboration. And your drivers? They need to know what’s changing and why.”

He even created a Fleet Advisory Board at Unilever, including drivers and managers at all levels, to share feedback.

“We talked about everything, including vehicle selection, safety, mileage, and technology. It helped everyone feel heard, and it made my job easier,” he said.

The Power (and Peril) of Fleet Data

Telematics might be one of the biggest game-changers in Cytowicz’s career.

“The amount of information we get now is mind-blowing,” he said. “But it’s easy to drown in it. You have to set benchmarks and know what metrics really matter.”

He encouraged fleet leaders to take a measured approach, recommending fleet managers “don’t chase every new piece of data or tech just because it’s there. Focus on what helps your people, improves safety, and strengthens your fleet’s financial position.”

Motivation in the Marathon

Fleet management isn’t for the impatient, and Cytowicz knows it.

“It’s not a sprint; it’s a marathon,” he said. And, just like runners get the runner’s high, he shared a clever analogy: “Watching everything come together, from policies to partnerships to vehicles, that’s the ‘fleet manager’s high’ for me. It’s seeing how all the pieces fit.”

Even after decades in the fleet business, he remains motivated by connection. 

“We call this the fleet family for a reason,” he added. “I’ve had friends in this industry for over 30 years. We support one another, even across competing companies. That’s rare.”

Advice for the Next Generation of Fleet Managers

Cytowicz’s advice to newcomers is simple and heartfelt.

“Understand the process,” he said. “Ask questions. Learn from others. And don’t be afraid to reach out.”

He encourages joining associations like the NAFA Fleet Management Association and the Automotive Fleet & Leasing Association (AFLA), as well as staying connected to the wider fleet community.

“The relationships you build early on will carry you through your career. They’ll become your support network,” he said.

And when it comes to the future? He’s optimistic (and ever practical).

“Technology will keep changing, but don’t lose sight of safety, cost management, and people,” Cytowicz said. “Stay current, stay curious, and keep your drivers at the center of every decision.”

The Final Word

Oleg Cytowicz may joke about starting in the “abacus era,” but his perspective is anything but outdated. His story reminds us that, behind every fleet program, policy, or platform, it’s still people — not just vehicles — who drive the real change.

“I’ve been fortunate to experience so much in this industry,” Cytowicz said. “If anyone needs help or advice, reach out. Nothing makes me happier than helping someone make a tough decision a little easier.”