At Skift’s Data + AI Summit, Wil Slickers sits down with Rob Drotar, Industry Principal at Thoughtworks, to unpack one of the next major shifts facing travel: the rise of AI agents as a new customer interface.

The conversation moves beyond chatbots and automation to the bigger commercial question: what happens to customer ownership when an AI agent starts discovering, comparing, recommending, and potentially booking travel on behalf of the traveler?

Rob explains why business-to-agent matters, how OTAs and suppliers may approach the shift differently, and why direct booking strategies could face new pressure. The discussion also covers digital twins, data orchestration, legacy modernization, and what travel companies need to make their products agent-ready.

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Episode Chapters:

Recorded at Skift's third annual Data and AI Summit in New York City, David Peller sits down with Teresa Mackintosh, CEO of Aven Hospitality, to talk about what it actually looks like to build an AI-first company from the ground up.

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00:00 Summit Setup

Intrepid Travel is proving that you can build a mission-driven travel company and still be more profitable than ever.

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Destination marketing is changing fast, and this session makes it obvious why.

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AI is becoming the new front door to travel, and consumer behavior is moving faster than most companies can keep up.

In this Skift Take Sessions episode, Wil Slickers sits down with Skift Head of Research Seth Borko to break down what matters most from Rafat Ali’s Skift Global Forum conversation with Sierra AI CEO Bret Taylor, who also chairs the OpenAI board.

Wil and Seth unpack why distribution is the first battleground, why travel brands need to start building and cleaning up their data now, and why the real upside is not just cost-cutting but loyalty and revenue growth through personalized service at scale.

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OYO is now Prism, and the strategy is bigger than a name change.

In this Skift Take Sessions episode, Wil Slickers sits down with Skift hospitality reporter Sean O’Neill to break down what Prism CEO Ritesh Agarwal is really building after years of pivots: a business that is now essentially split between India and the U.S., anchored by the Motel 6 acquisition and a push to modernize the budget experience with a tech rebuild. 

Wil and Sean unpack why “iconic” matters for Motel 6 despite its baggage, what a real turnaround would require (digital, standards, and property churn), and why Prism is doubling down on economy and extended stay through Studio 6 while much of the industry chases upscale. They also dig into the IPO signal, with Ritesh framing the board’s active evaluation of an India listing and why India’s travel market momentum is part of the timing.

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In this Skift Take Sessions episode, Wil Slickers sits down with Skift hospitality reporter Sean O’Neill for a quick, high-signal setup on what mattered most from IHG CEO Elie Maalouf’s Skift Global Forum appearance.

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Alaska Airlines is in one of the most important transition moments in its modern history, and it is happening under real operational pressure.

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This episode starts with a quick setup conversation between Wil Slickers and Skift’s airlines editor Gordon Smith, teeing up why this JetBlue session hits differently: it opens with a real-time operational disruption and a leadership test you cannot spin your way around.

Then we roll into Gordon’s on-stage conversation from Skift Aviation Forum with JetBlue CEO Joanna Geraghty, covering what happened, what JetBlue learned, and how the airline thinks about making high-stakes calls when customers only remember the day something breaks.

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If AI becomes the front door to travel, who wins and who pays?

Wil Slickers sits down with Dennis Schaal for a sharp, no-fluff breakdown of the biggest takeaways from Skift Global Forum, including the question everyone is asking: Is ChatGPT a paid marketing channel yet, or just the start of a new distribution shift?

Dennis and Wil unpack what matters for the future of travel discovery, how monetization pressure could reshape the funnel, and what it means for platforms like Booking when the interface changes.

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