Building a data program isn't all about the tech—it's about getting people to actually work together. Carlos Rivero shares what it was really like starting as Virginia's first Chief Data Officer with no team, no budget, and a lot of skeptical agencies. He talks about how he learned to be more of a "people wrangler" than a data expert, turning critics into allies and figuring out that most of the job was just getting everyone on the same page.

Ever wonder why so many promising tech pilots never make it past the starting line? In this episode, Sid chats with Jonathan Alexander about breaking free from “pilot purgatory” and actually scaling innovation. From cavemen pushing carts with square wheels to global rollouts of cutting-edge solutions, Jonathan brings stories, strategy, and wisdom about how to get things done in a giant enterprise. They dive into building business cases that don’t flop, why change management beats the perfect tech stack, and how to avoid getting stuck with great ideas that go nowhere.

Leading complex IT systems in a major city demands more than technical know-how—it requires a shift from individual success to team achievement. Summer Xiao, Deputy CIO of Houston, shares her journey from "I" to "we," discussing the crucial transition from "doer" to "facilitator," the importance of shared ownership in large projects, and how team performance reflects directly on leadership.