What Does a Real Fleet Career Look Like?
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This article is based on a recent episode of The Fleet Success Show podcast. Watch the full episode here:
Q: Who is Scott Conlon, and why should fleet professionals know his name?
A: Scott Conlon is a fleet unicorn. He’s done nearly everything: from student bus mechanic at the University of Maryland to National Fleet Manager for the U.S. Forest Service with a fleet of 18,000 vehicles, 5,000 pieces of equipment, and 23,000 fleet credit cards.
His career is a roadmap of what’s possible in fleet, but also a wake-up call for what’s missing. From managing compressed natural gas (CNG) buses to conducting right-sizing studies for federal agencies, Scott's seen it all. And through it, he's developed a deep conviction: fleet must be recognized as a strategic, professionalized career path.
Q: What’s broken about the fleet management career pipeline?
A: There is no pipeline, and that’s the problem.
Most fleet leaders don’t plan to be fleet leaders. They arrive through technical work, military experience, or accidental opportunity. Scott calls out this flaw: there’s no standard pathway from technician to supervisor to director.
In other words, while other industries have defined training, education, and career ladders, fleet remains fragmented. Promotions often come without leadership training, leaving talented people unprepared and unsupported.
Q: So how did Scott learn to lead?
A: By jumping in the deep end, and learning to swim fast.
At 27, Scott was managing two 24/7 transit shops in Montgomery County, MD, overseeing 36 mechanics and six shifts with virtually no formal training. Instead, he pulled from his military background, watched great leaders, avoided bad ones, and taught himself how to manage people, processes, and performance.
But as he said on the podcast: “It shouldn’t have to be that way. We need structured development paths. We need education programs that aren’t just for technicians — but for leaders.”
Q: What’s the impact of poor fleet education?
A: High turnover. Burnout. And underperformance at scale.
Without professional development, fleet managers struggle to justify budgets, interpret data, or communicate their strategic value to executives. That creates a vicious cycle: leaders don’t trust fleet, fleet can’t get resources, and services suffer.
Meanwhile, the best people leave for industries that offer training, mentorship, and career mobility.
Q: What’s Scott’s vision for fixing it?
A: A three-part professionalization plan:
- Create industry-standard leadership training.
From front-line supervisor to fleet director, every level should have a development path. - Partner with higher ed.
Universities should offer fleet-specific programs, just as they did for nursing and tech when those fields hit crisis points. - Elevate the profession.
Fleet leaders should be at the executive table — not buried three layers deep in public works.
Q: What was Scott’s most challenging fleet role?
A: National Fleet Manager for the U.S. Forest Service.
- Fleet size: 18,000 vehicles, 5,000 equipment assets
- FTEs: 175+ across the U.S.
- Fire fleet: Over 3,500 fire vehicles including wildland trucks, tenders, and patrol units
- Complexity: Matrixed reporting structure, global operations, and federal compliance
He wasn’t just overseeing trucks — he was managing supply chains, stakeholder politics, disaster readiness, and a national data strategy.
Q: What does Scott love most about fleet?
A: The variety. “It’s a Renaissance career,” he says.
One day you're reviewing lifecycle analytics. The next, you're rewriting policy, training a new tech, or just wrenching in your own garage for fun. Fleet is one of the last remaining careers where technical knowledge, leadership, analytics, and field service intersect every day.
Q: What’s Scott’s message to fleet newcomers?
A: “We need you. This industry will be here forever, and if you’ve got talent and hustle, you’ll never be out of work.”
The opportunity is massive. The tools are finally catching up (like RTA’s fleet management software). But the career path needs champions, people who want to build a stronger, smarter, more respected industry.
And Scott’s just getting started.