In this episode of Ted Listens, I sit down with Brynn Michelich, Chief Operating Officer at Jellyvision, the Chicago tech company behind the wildly successful benefits-education platform ALEX. Brynn shares the fascinating evolution of Jellyvision, starting with educational films in the late ’80s, moving through the CD-ROM gaming era (yes, including You Don’t Know Jack), and ultimately becoming a leading HR-tech company helping millions of employees understand and use their benefits.
From transitioning a services business into a scalable product, to navigating healthcare complexity, AI adoption, employee communication, and hybrid-work culture shifts, Brynn offers candid insights on leadership, operations, and what it really takes to build a company that blends behavioral science, empathy, humor, and technology.
If you're an operator, founder, HR leader, or simply love great Chicago startup stories, this is a conversation you won’t want to miss.
More on Jellyvision: https://jellyvision.com/
More on my company: https://cliquestudios.com/
