Kyle Waldrep, JLL Technologies

Chip sits down with Kyle Waldrep, Director of Product Management at JLL Technologies and Founder of dottid, to talk about entrepreneurship, technology adoption, and the rapid evolution of commercial real estate.

Kyle shares insights on building and selling a company through challenging market conditions, how AI is reshaping real estate workflows, helping brokers become more strategic advisors, and creating the right balance between innovation, scalability, and governance. He also reflects on the leadership lessons he learned along the way, including the importance of humility, listening, hands-on learning, and continuing to move forward.