Founders Should Hire Young CEOs for AI Transformation

Owen McCabe's transformation of Intercom into an AI-first company demonstrates that radical change requires decisive, founder-led action in the face of disruption.

When Owen returned to Intercom, the company was approaching zero net new ARR after five quarters of sequential decline. Just one month after his return, ChatGPT launched, presenting both a threat and an opportunity. Rather than making incremental changes, Owen took a decisive, top-down approach to transformation that fundamentally reshaped the company's direction, culture, and performance.

The core of Owen's leadership philosophy is that greatness comes from CEOs willing to make brave, hard decisions and own the results. He believes that founder-led companies perform substantially better because founders have the moral authority and willingness to take risks that professional CEOs often avoid. When faced with AI disruption, he didn't seek consensus but instead made unilateral decisions about strategy, culture, and resource allocation.

This approach required significant cultural transformation. Owen rewrote company values to create what he called "a sharp knife to cut out the parts of the company that wouldn't be effective." He implemented performance processes that scored employees not just on results but on alignment with these values. This led to approximately 40% employee turnover, but resulted in an organization filled with "the most incredible entrepreneurial brave inspiring happy individuals."

For leaders navigating AI disruption, Owen's message is uncompromising: "You don't have a choice. AI is gonna disrupt in the most aggressive violent ways. If you're not in it, you're about to get kicked out of all of it." He emphasizes that competing in AI requires actual AI talent, empowering young talent, and a willingness to work extraordinarily hard—matching the intensity of AI startups run by founders in their twenties who are "literally working twelve hours a day, literally 365 days a year."

For individual contributors, the implications are clear: align yourself with companies and leaders willing to make hard decisions and embrace transformation. The most successful teams will combine human creativity with AI capabilities, requiring both technical skills and the ability to configure, monitor, and manage AI systems. Owen predicts organizations will become smaller and flatter, with a complex mix of humans and agents working together.

Perhaps most importantly, Owen suggests that leaders must honestly assess whether they're willing to make the necessary changes and match the intensity required to win in AI. His provocative advice: if founders aren't willing to roll up their sleeves and work as hard as younger competitors, "hire a kid. You can be a chairperson... have a lot of fun, you can mentor the kid, hire a kid because you're in the wrong job buddy."