#131 - AI Product Strategy: When to Build and When to Wait with Matthias Keller // CPO @ Kayak
alphalist.CTO Podcast - For CTOs and Technical LeadersShow Notes
Matthias Keller, Chief Product Officer at Kayak, shares hard-won lessons about AI product strategy and knowing when to invest in emerging platforms. With a PhD in computer engineering from ETH Zurich and 12 years at Kayak, Matthias has lived through multiple waves of AI hype—from Alexa voice skills in 2016 to today's LLM revolution. He discusses the strategic calculus of early platform bets, the painful lessons from experiments that didn't pan out, and how to recognize when technology has truly shifted. The conversation covers navigating distribution challenges when competing with giants like Google and ChatGPT, balancing first-mover advantage with execution realities, and how LLMs are democratizing AI development for engineering teams. Matthias emphasizes the critical framework: "if you build it, they may come—if you don't build it, they won't come."
More from alphalist.CTO Podcast - For CTOs and Technical Leaders
Raffi Krikorian has built teams at scale: platform engineering at Twitter, Uber's self-driving center, and the Democratic National Committee, where he was its first CTO. Today he's CTO of Mozilla, working to make AI as open as the web, and on the side he runs three rotating Claude Max subscriptions and a GPU in his closet.
Chris Wysopal was one of the first hackers to go public. As "Weld Pond" at the L0pht hacker collective in Boston, he testified before the US Senate in 1998, where the group delivered the soundbite that they could take down the internet in 30 minutes. He also wrote the Windows version of Netcat. In 2006 he co-founded Veracode, which by his account has now analysed trillions of lines of code. Today he's the company's Chief Security Evangelist.
Charles Guillemet has spent nine years building Ledger's security organization from scratch — first as the founder of The Donjon, Ledger's in-house offensive security research team, then as CTO overseeing security for a company safeguarding roughly 20% of the world's crypto (per Tobi's intro framing).
Sponsored by Blocks: Save at least 20% on your AWS costs with AI-powered optimization and enterprise discounts. Get your free Cloud Check at https://blocks.cloud/alphalist?utm_source=alphalist&utm_medium=podcast&utm_campaign=blocks-podcast-2026
Sponsored by Blocks: Save at least 20% on your AWS costs with AI-powered optimization and enterprise discounts. Get your free Cloud Check at https://blocks.cloud/alphalist?utm_source=alphalist&utm_medium=podcast&utm_campaign=blocks-podcast-2026