#131 - AI Product Strategy: When to Build and When to Wait with Matthias Keller // CPO @ Kayak

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."

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#131 - AI Product Strategy: When to Build and When to Wait with Matthias Keller // CPO @ Kayak is an episode from alphalist.CTO Podcast - For CTOs and Technical Leaders by Tobias Schlottke - alphalist CTO Podcast.

This episode is 51:41 long.

This episode was published on Nov 13, 2025.

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