Zendesk’s CEO got real-life AI lessons from vibe coding an app with his son

In today’s CEO Daily: Zendesk’s CEO on using AI firsthand.

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Good morning. Zendesk CEO Tom Eggemeier says he’s been telling his kids since 2023 that AI will be “bigger than the printing press, the internet, the Industrial Revolution,” and that they’d fall behind without it. Earlier this year, his son Will, a Boston College senior and basketball player who’s majoring in history with a minor in business, called his bluff. Will suggested they work together on a predictive analytics app to help college athletics programs find players in the NCAA transfer portal before richer schools do. “We wanted to create something that might be able to level that playing field a little bit,” Will told me during a recent interview alongside his dad. Tom helped design the interface, and they named it Underdog AI.

At first, everything was easy. “We were vibe coding, and it was exciting because of the cool features that were coming out,” Tom said. But Will knew something was off when the AI made recruitment suggestions that didn’t sound right. Speedy development created technical debt in areas from security to API protocols, and hours of debugging that reinforced that there are no shortcuts to making software seamless and secure. Two college basketball general managers told them the app matched about 70% of what’s already for sale; Will also can’t sell to rival schools while he’s on BC’s roster, so he’s tweaking the project until he graduates.

Will says he loved seeing his father work through problems in real time. He’s hoping to build a career in the sports business and believes knowing how to deploy AI is essential to success. He credits his dad with helping him develop grit, citing “suck it up” as a favorite line.

Tom........

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