Why Deliberate Practice and Sales Coaching Develop Better Freight Reps

Practice in freight sales doesn't get enough attention. Most reps learn on live calls — which means customers are absorbing the cost of their development. The organizations that invest in structured practice, role-playing, and coaching create a different kind of rep: one who has already failed at the hard parts in a low-stakes environment before they're in front of an actual shipper. In this episode of The Journey Podcast, Will Jenkins sits down with Gabe Ribeiro, Senior Director of Partnerships and Marketing at Hey Bubba, to make the case for practice as a strategic investment in freight sales performance.

Gabe brings perspective from both freight tech and marketing: how his background in those spaces shaped his understanding of how sales teams actually learn, and why the gap between what companies say about training and what they actually do shows up directly in their results. He talks about active listening as a learnable skill — not a personality trait — and how role-playing creates the reps to develop it without risking a real account.

The conversation covers building a practice culture inside a freight sales organization: what it takes from leadership to make deliberate practice feel like a competitive advantage rather than a remediation exercise, and why the teams that normalize coaching and feedback consistently produce better reps than those that treat training as something you do when someone is underperforming. Gabe also shares how he thinks about handling objections in freight sales and what practice specifically prepares reps for that live calling doesn't.

For freight organizations investing in sales training and development, explore The Freight Academy or build practice reps with Journey's AI Sales Coach.