Skift Data & AI Summit 2026 Roundtable: When AI Knows Travelers Better Than Brands Do, Who Owns the Relationship?

This sponsored content was created in collaboration with a Skift partner.

A traveler who’s spent years loyal to the same hotel chain can still feel like a stranger when checking in at the front desk. Meanwhile, an AI assistant may already know their favorite destinations, preferred room type, and spending habits.

That possibility sat at the center of an attendee roundtable hosted by Mindtrip at Skift Data + AI Summit 2026. As AI becomes a more common starting point for travel planning, valuable traveler insights are increasingly sitting outside the systems traditionally controlled by hotels, airlines, and online travel agencies.

Underlying the discussion was the question: If AI knows travelers better than brands do, who owns the relationship?

Led by Tom Krackeler, chief product officer at Mindtrip, the discussion brought together leaders from travel technology, hospitality, destination marketing, payments, and luxury travel to explore how personalization is changing the path to purchase.

Below are key themes that emerged from the conversation.

The Battle for Traveler Context

Krackeler framed the conversation around a question that’s becoming increasingly relevant as AI becomes part of the travel planning process: What if personalization is no longer about predicting what travelers might want, but about understanding who they are?

At Mindtrip, he said, the goal is to build a persistent picture of the traveler that carries across the planning journey, helping people sort through choices, compare options, and make decisions that better reflect their preferences and priorities.

Participants returned repeatedly to the idea that AI is changing what personalization means in practice. Travel companies have historically relied on loyalty profiles, booking histories, and broad customer segments to anticipate traveler preferences, but the emerging generation of AI tools now points toward something more fluid.

The discussion centered on the possibility that travel systems could gradually accumulate an understanding of a traveler over time, drawing on factors such as destination preferences and spending habits, loyalty memberships, travel companions, and personal constraints.

Several participants noted that travelers are increasingly sharing information with AI assistants that may never make their way into an airline’s reservation system or a hotel’s customer database. A conversation about family travel, dietary preferences, budget concerns, or vacation ambitions may happen entirely outside the channels where travel brands have traditionally gathered customer insights.

Because travel decisions are interconnected, a richer understanding of the traveler can help AI systems evaluate tradeoffs across an entire trip rather than treating each decision as an isolated transaction.

That leaves travel brands with a difficult question: How do they remain relevant when they no longer hold the most complete picture of the traveler?

As the discussion evolved, attention shifted to the issue of trust.

Several participants argued that travelers should have greater control over their personal information and preferences. One idea that generated significant discussion was the concept of a portable profile that travelers could choose to share with trusted brands, suppliers, or advisors.

Underlying this was a concern about how future AI platforms will operate. Participants drew comparisons with the evolution of search engines and questioned whether AI-driven discovery could eventually become influenced by commercial priorities.

The group agreed that personalization only works when trust exists. Travelers may be willing to share more information if they believe it will help them make better decisions. The participants envisioned AI systems acting less like search engines and more like trusted advisors that represent the traveler’s interests throughout the planning process.

While most of the conversation focused on the future, participants also pointed to a more immediate challenge.

Travel brands already collect enormous amounts of customer information through loyalty programs, booking histories, and past interactions. However, many struggle to translate that information into meaningful experiences.

Hospitality was a recurring example. Participants noted that major hotel brands often possess extensive guest data but frequently fail to surface it when it matters most. Recognition at check-in, personalized service, and relevant recommendations remain inconsistent despite years of investment in customer data platforms and loyalty programs.

The consensus was that the problem is rarely a lack of information. More often, the issue is that valuable customer insights remain trapped inside disconnected systems and never reach the people who can use them.

The challenge becomes even greater when traveler context extends beyond a single brand. A hotel may understand a guest’s stay history, while an airline understands flight behavior, but travelers increasingly expect experiences that reflect the broader context of their trip.

One theme surfaced repeatedly throughout the discussion: travelers are overwhelmed by information.

Consumers have access to more travel content, reviews, recommendations, and choices than ever before. Participants suggested that the next generation of AI tools may create the most value not by providing more information, but by helping travelers cut through the noise.

Attendees described a future in which AI serves as a decision layer, helping travelers evaluate options, weigh trade-offs, and identify the choices most relevant to them.

The biggest takeaway from the discussion was a consensus that the rules of personalization are changing.

The industry has always focused on collecting more data, refining customer segments, and improving targeting. AI is shifting the emphasis toward understanding travelers over time.

As AI capabilities continue to evolve, that context may become increasingly important not only for personalization but also for execution. The same understanding that helps a traveler evaluate options today could eventually help coordinate, manage, and adapt trips on their behalf.

For Mindtrip, the promise of AI lies in its ability to build context. A traveler planning a weekend getaway today and a family holiday six months from now may appear to be making separate decisions, but each choice reveals something about preferences, priorities, and habits. The challenge, and the opportunity, is turning that knowledge into guidance that grows more useful when the next decision arrives.

To learn more about how Mindtrip is rethinking travel planning with AI, visit mindtrip.ai

This content was created collaboratively by Mindtrip and Skift Studio.