Tom Alexander has spent his career at the intersection of people, policy, and technology — from the mayor’s office in Chicago to COO of 1871 and now CEO of Holistic. In this conversation with Glenn Gow, he reveals why internal communication is the true cheat code for scaling, why perks like snacks and ping pong are distractions, how leaders sabotage themselves by ignoring culture, and how AI can help CEOs turn employee insights into real action. This is a powerful episode on the people side of growth and what it really takes to build companies that last.