What a Freight Career Across Brokerage, Trucking, and Tech Teaches You

Most freight professionals know one side of the industry well. Todd Waldron knows all of them. Over a 17-year career, he's worked inside CH Robinson's brokerage operation, opened JB Hunt's Minnesota brokerage branch, transformed a 40-year-old trucking company, and now shapes carrier experience at TruckStop. In this episode of The Journey Podcast, Will Jenkins sits down with Todd to talk about what that breadth of experience teaches you about how freight actually works — and what leaders can learn from seeing every side of it.

Todd talks about each chapter of his career with the specific lessons it delivered. At CH Robinson, he learned the competitive intensity and operational discipline of large-scale freight brokerage. At JB Hunt, the challenge of building a new market from scratch inside a large organization. At the trucking company, what it actually looks like to try to modernize a legacy business with decades of established culture and operational habits. And at TruckStop, the technology perspective — understanding carriers' needs from the platform level.

The conversation covers what each chapter built that the next one required: the skills and perspectives that cross from brokerage to trucking to technology, and the ones that are genuinely different enough to require relearning when you change positions in the freight ecosystem. Todd also shares what he thinks freight leaders who've operated on only one side of the industry systematically misunderstand, and why that misunderstanding shows up in their decisions.

For freight professionals navigating career development across the industry, explore Journey's executive search or freight consulting services.