- In today’s CEO Daily: Zendesk’s CEO on using AI firsthand.
- The big leadership story: Nvidia probes CEO Jensen Huang’s affair with a suspected spy.
- The markets: Mostly up globally after a wild week of trading.
- Plus: All the news and watercooler chat from Fortune.
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 how 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 gained as much or more from the experience, saying it made him “a better leader for our R&D organization, our product, and AI.” The experience changed how Tom thinks about AI, from investing heavily in employees’ AI skills to focusing on how AI agents help people cut expenses, time, complexity, or solve other real-world problems.
Some lessons he’d share with other CEOs?
Use the technology yourself. Tom used a personal agent to renegotiate his insurance coverage, internet bill, mobile plan, and subscriptions, and says he’s “a little embarrassed to say it saved me $3,150 a year.” Having trained ChatGPT Work to write in his voice, he noticed that it kept ignoring his instructions to avoid contractions, which he thinks are harder for non-native English speakers to understand. “That recurring mistake has led me to think more deeply about how memory and skills affect our products and internal use of AI.”
Also, keep hiring young employees; AI natives bring a fluency that creates an interesting dynamic alongside experienced workers. Understand the anxiety around AI while helping people gain skills. Create projects that put AI to work on real problems. And if your kids want to build something with you, do it. Contact CEO Daily via Diane Brady at [email protected]
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