From Tech Support to Freight Tech CEO: Curiosity, Mentorship, and Leadership

Cameron Robertson didn't plan to run a freight technology company. He started in tech support. In this episode of The Journey Podcast, Will Jenkins sits down with Cameron — CEO of 3PL Systems — to talk about a career path built on curiosity, mentorship, and the willingness to step into roles before he felt fully ready for them.

Cameron covers his early career decisions and the specific moments that redirected his path toward logistics technology. He talks about what it meant to take over as CEO of a freight software company — not just the operational transition, but the identity shift required to lead a team that had worked with his predecessors and had expectations shaped by a different kind of leadership. He's honest about what he got wrong early and what he learned from it.

The conversation covers the COVID-19 pandemic as a business leadership challenge: what it looked like to navigate a freight technology company through an unprecedented market disruption as a relatively new CEO, what decisions he made that held up in hindsight and which ones he'd make differently, and how the pandemic accelerated some of the technology adoption trends that are still shaping how freight brokerages operate today.

Cameron also shares his perspective on AI's current role in freight technology: where he sees genuine value, where he sees the hype outrunning the reality, and what 3PL Systems is focused on to serve freight brokers in a market that's more technology-competitive than it's ever been.

For freight technology professionals and logistics leaders, explore Journey's freight consulting or executive search for freight tech organizations.