Selling freight technology at a startup is not the same job as selling it at an established company. The product is still being built. The brand has no recognition. The sales process doesn't exist yet, or it exists in someone's head rather than in a CRM. The reps who thrive in that environment are wired differently from those who perform best when the infrastructure is in place. In this episode of The Journey Podcast, Will Jenkins sits down with Kyle Richards, VP of Sales at CloneOps, to talk about what startup freight tech sales actually requires.
Kyle's perspective is grounded in direct experience: he's navigated the transition from the structure and resources of a larger organization to the speed, ambiguity, and ownership required at a startup. He talks about the mindset shift specifically — how to operate effectively when you're building the plane while flying it, and why reps who need a playbook to perform tend to struggle in startup environments while those who can write the playbook as they go tend to thrive.
The conversation covers how freight sales strategy shifts in a startup culture compared to larger organizations: the faster decision-making, the closer relationship between sales and product, and the importance of teamwork in an environment where there's no department to hand off to. Kyle also talks about adaptability as the core competency — the willingness to change your approach based on what the market is telling you rather than what the strategy deck says.
For freight sales professionals evaluating startup opportunities or freight tech companies building their first sales teams, explore Journey's freight consulting or contingent recruiting for logistics organizations.
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