Freight brokerage sales and freight technology sales share an industry but operate very differently. The buying process, the stakeholders, the sales cycle, and the value conversation are all distinct enough that reps who transition from one to the other without recalibrating often struggle. In this episode of The Journey Podcast, Will Jenkins sits down with Kyle Richards, VP of Sales at CloneOps, to break down what makes freight tech sales different and what it takes to succeed in it.
Kyle covers the first major difference: the buyer. In brokerage, you're usually selling to operations and logistics professionals. In freight tech, you're often navigating a buying committee that includes IT, operations, finance, and C-suite stakeholders — each with different concerns and different definitions of value. He talks about how to map a freight tech buying group, identify champions, and build the internal consensus that gets a deal to close.
The conversation gets into the role of AI in logistics specifically: how AI-powered freight tools are changing what buyers evaluate, what questions they ask, and what proof they need before they're willing to commit. Kyle shares how sales reps in freight technology can demonstrate real value rather than AI buzzwords, and what the adoption conversation looks like when you're asking a freight organization to change how their team operates.
This episode is essential for freight tech sales professionals and anyone considering the move from brokerage to technology sales.
For freight professionals navigating tech sales transitions, explore Journey's freight consulting or freight tech executive search.
.webp)
