In this episode, Matt sits down with Gary Dowdy, Chief Technology Officer at Trinity Logistics, one of North America's leading freight brokerage firms. Gary shares his fascinating career journey through warehouse automation, mobile banking, and seven years helping build the JB Hunt 360 digital freight marketplace before landing at Trinity. Together, they explore how Trinity is leveraging cloud infrastructure, agentic AI, and voice automation to transform freight operations — handling over 80,000 minutes of AI carrier conversations in a single month. Gary also offers candid insights on governing AI adoption, keeping data ready for what's next, and why strong leadership and human connection remain the most important ingredients in an increasingly automated industry.