AI That Plans, Not Just Chats: What to Expect from KAYAK at the Skift Data + AI Summit

As Chief Product Officer at KAYAK, Matthias Keller is at the forefront of reshaping how millions of travelers plan their trips. With over a decade of leadership at one of the world’s most innovative travel search engines, Keller has helped pioneer the integration of artificial intelligence into travel.

His work on KAYAK.ai is leading the shift from reactive, form-based search to proactive, personalized travel experiences. At the Skift Data + AI Summit, Matthias Keller will unpack the emerging technologies and real-world strategies that are turning AI into a true co-pilot for travelers, not just another interface.

Ahead of his session, Keller offers a glimpse into how smarter AI is reshaping travel and what lies ahead for the industry.

“At KAYAK, we see AI as a way to move beyond the traditional constraints of predefined search forms and toward truly intelligent, personalized travel planning.”

“With KAYAK.ai, prompts help us better understand what a traveler wants — not just what they click — enabling more relevant responses. As agent capabilities evolve, reasoning and planning open the door to smarter, more contextual recommendations that make trip planning faster, easier, and more tailored to the individual.”

“It’s still early days, and everyone is experimenting — but one thing is becoming clear: simply adding AI for the sake of it doesn’t create real value.”

“Too often, the industry treats AI as a surface feature, like adding a chatbot. But meaningful impact comes when AI powers useful capabilities across the full journey. At KAYAK, we believe AI should do more than respond — it should reason, plan, and simplify complexity. That’s where it becomes truly valuable to users.”

“We’re closely watching the evolution of Agentic AI — systems that don’t just provide information, but take action on a traveler’s behalf. The ability to delegate planning, booking, and even post-booking management to a trusted AI agent has the potential to transform the travel experience.”

“There’s also an interesting space emerging around 'computer-use' agents, like OpenAI’s Operator, which can interact with third-party tools or websites on a user’s behalf. While still early and relatively slow, this technology could become a powerful way to gather information and complete transactions in real time.”

“If we had to place a big bet, it would be on AI’s evolving ability to perform complex reasoning — moving beyond recommendations to taking action on behalf of the user. The potential to plan and book multi-destination trips through a single intelligent interface has huge potential.”

“One area we’re also excited about is how improved reasoning capabilities are being applied to geospatial challenges. For example, we’ve already seen promising progress in reverse-geocoding from images. Applying that capability to travel — such as identifying optimally located hotels based on user preferences or dynamically mapping multi-stop itineraries — could significantly enhance how people plan their trips.”

Don’t miss Matthias Keller’s session, where he’ll reveal how AI-powered smarter search and agentic travel planning are redefining the future of travel journeys. This is your chance to hear firsthand from the industry’s leading innovators about the technologies shaping tomorrow’s travel experiences. Secure your spot now and be part of the pivotal conversation transforming the travel industry.

June 4, 2025 - NEW YORK CITY