Brynn Michelich of Jellyvision

I got a chance to sit down with Brynn Michelich, COO of Jellyvision, to unpack one of the most unique company evolutions in Chicago tech. Brynn traces Jellyvision’s 35-year journey from an educational media company in the late 1980s, to a CD-ROM gaming studio (including the cult hit You Don’t Know Jack), to a creative agency, and ultimately to the creators of ALEX, a benefits education platform used by millions of employees across the country.

Brynn explains how Jellyvision’s throughline has always been the same: educate by entertaining, reduce complexity through conversational design, and meet people where they are. The episode dives into the early days of transitioning from services to a scalable product, the challenges of teaching people about healthcare and benefits, and how ALEX leverages tone, personality, and behavioral science to make one of the most confusing topics feel human and approachable.

The conversation also explores Brynn’s role leading business operations across the company, including everything from HR to the PMO to internal systems. She offers candid insights into delegation, culture building, succession planning, and why great companies rely on people who aren’t afraid to say, “I don’t know, but I’ll figure it out.” Ted and Brynn discuss hybrid work, employee communication, the importance of feeling connected to coworkers, and what employers often misunderstand about benefits and the modern workforce.

Ultimately, this episode is a behind-the-scenes look at a company that blends humor, empathy, and technology to solve real-world problems.

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