Cloudflare CEO Matthew Prince on AI, Local Media and the Future of Search
Photo Credit: Jason Bollenbacher via SXSW
Cloudflare CEO Matthew Prince, right in main photo, came to South by Southwest with big questions about the future of work, media and the internet itself: What happens inside companies when some employees fully embrace AI while others resist it? What replaces a local journalism business model that no longer works? And how should brands adapt when the “customer” navigating their websites may increasingly be an AI agent rather than a human? Those themes shaped Prince’s on-stage conversation with Stephanie Mehta (left in main photo), CEO and chief content officer of Mansueto Ventures, parent company of Inc. and Fast Company, during their SXSW session, “The Internet After Search.”
The Messy Middle
Prince spoke about a workforce problem he doesn’t yet have a clean answer to. Inside organizations everywhere, including his own, a divergence is emerging. A portion of employees have embraced AI tools and are using them to dramatically multiply their output. Another group hasn’t. They’re proud of their craft and while less efficient, they do a decent job and produce solid work. And right now, both groups are largely paid the same.
He called this gap the “Messy Middle” — the cohort of experienced and capable workers who have not integrated AI into their workflows, even as colleagues using the tools are operating at two or three times their previous capacity. On one end are the early adopters. On the other are younger workers entering the workforce already fluent in AI.
The challenge for organizations, Prince suggested, is figuring out what happens next — when productivity expectations, performance and compensation begin to diverge.
“That’s what keeps me up at night,” Prince said. It’s not a technology problem. It’s a management, culture and compensation problem — and most organizations haven’t begun to reckon with it seriously, Prince said. Not all CEOs are admitting this publicly, he said, but they’re looking for ways to address it.
“The game has changed,” he said.
Buying the Local Paper
Prince and his wife Tatiana made headlines in 2023 when they acquired The Park Record in Park City, Utah. On stage, he used that decision as a window into something he believes deeply: the traditional media business model isn’t just struggling, it’s structurally broken and won’t be fixed by incremental change. He said the answer is not paywalls, subscriptions and ads.
“The future model will change radically,” he said, noting licensing content to AI will be a large part of the solution, as local news is a valuable part of what AI offers in search results.
When Your Customer Becomes a Bot
Web traffic, the Cloudfare CEO argued, is shifting, faster than most brands realize, from human visitors to AI agents acting on behalf of humans. By 2027, bot traffic will exceed human traffic in search, he said.
The implications are significant. Prince said a human consumer might visit five websites before making a purchase decision. An AI agent might visit thousands, in seconds, with no emotional response to your homepage design, your brand story or your banner ad. He said agents don’t notice branding. They don’t click on ads. They evaluate and move on before presenting the best deals to the end-user human who trusts the AI output.
For marketing and PR professionals, this is an active restructuring of how trust and visibility get built online. The brands that figure out how to be legible to agents, not just appealing to humans, may have a significant early advantage.
Prince didn’t offer a playbook. Instead, the former ski instructor turned billionaire tech CEO focused on mapping the terrain ahead. Where AI, media and marketing are all changing faster than anyone fully understands.
Capitol Communicatoris a sister company of CommPRO.
