Freight Technology Leadership Lessons from Startup to Scale

Kary Jablonski didn't start in freight. She started as a consultant at Deloitte, moved into product and market expansion roles at Uber, and eventually found her way to Trucker Tools, where she now serves as CEO. In this episode of The Journey Podcast, Will Jenkins sits down with Kary to talk about what a career built across very different industries teaches you about leadership — and what the lessons specific to freight tech leadership look like in practice.

Kary talks about her time at Georgetown studying economics and government, her early days at Deloitte where she learned how large organizations actually function, and the Uber years where she launched and scaled markets across the U.S. and internationally. Each chapter built something different — and she's clear-eyed about what transferred to her work in logistics technology and what required relearning from scratch.

The conversation covers her philosophy around uncertainty — not just tolerating it, but treating it as the default operating environment for anyone building something in a fast-moving industry. She talks about what good leadership looks like when you're running a freight tech company with a diverse team, long sales cycles, and a customer base that ranges from owner-operators to large fleet managers.

This episode is for logistics leaders and freight tech professionals who want a grounded perspective on what executive leadership in this industry actually demands.

Explore Journey's executive search for freight and logistics technology companies, or learn more through Journey's consulting services.