Travel Industry’s Quiet AI Talent Wars Are Heating Up

Every so often, a single LinkedIn job ad says more about strategy than a 40-page 10-K. Last week I dove into AI listings across travel, decoding four that reveal how the biggest brands are reorganizing around machine intelligence. Together they form a breadcrumb trail from C-suite power moves to nuts-and-bolts product work.

We’re calling this new series Skift AI Talent Tracker. Think of it as a recurring, detective-style column, scouring hiring boards for the real story behind corporate press releases about AI developments: raw signals, a quick take, and why it matters for the people who move the industry.

Below are four companies with my brief analysis, based on their recent LinkedIn job postings.

Royal Caribbean Group quietly promoted Matthew Denesuk, Ph.D., to Chief AI Officer, according to his LinkedIn profile, one of the first roles of its kind in travel. Can't wait to see how this plays out. We have RC Group CEO Jason Liberty on stage at Skift Global Forum 2025 in September; you can bet this will come up.

Who else among large or mid-cap public travel companies has hired a Chief AI Officer or equivalent? The only other ones I know are Brand USA, who put Janette Roush in that seat months ago, already ahead of the curve.

Theme parks are perfect AI sandboxes, closed, sensor-rich, and guest-dense. Universal Orlando Resort is hiring a head of AI, and it looks like they're just starting to explore its potential (presumably GenAI):

“The Director of Artificial Intelligence provides end-to-end technical leadership for AI and automation initiatives across the enterprise, navigating organizational vision, directing advanced ML solutions, and aligning AI efforts with broader strategic goals.”

Found this fascinating job posting from Marriott International, and you can read the tea leaves about their AI strategy. It’s hiring a Senior Director of Engineering & Architecture to lead the design of a centralized messaging platform orchestrating guest communications across call centers, hotel front desks, web chat, mobile apps, WhatsApp, SMS, iMessage, and more.

This centralized approach contrasts sharply with lots of small experiments happening at other chains, aligning precisely with what Marriott CTO Naveen Manga hinted at our Skift Data + AI Summit when he emphasized efficiency through centralization.

Here's another intriguing twist: it’s a temporary but full-time position. My guess? Marriott wants to rapidly build this infrastructure without navigating the internal approval red tape needed for permanent executive headcount. At $68–$112 an hour (~$142K–$232K/year before benefits), that's solid senior-tech money for hospitality.

All in all, fascinating.

Everyone assumes Booking Holdings is all-in on Booking.com as its AI flagship, attracting most resources and attention.

But here’s a surprise: Priceline is quietly staffing four heavyweight roles to build out Penny, its AI travel assistant most people haven't even heard of:

• Senior PM, AI Experiences – builds orchestration layer, memory & reasoning (mini-AutoGPT for travel).
• Staff Multimodal Product Designer – gives Penny voice, chat, touch & vision.
• Senior PM, Mobile AI – makes Penny feel native on iOS/Android, not bolted on.
• Senior PM, Conversational AI – fine-tunes personality, prompts, and emotional tone.

That’s the whole stack: brains, face, body, and soul.

Why Priceline? Being the underdog might give it room to experiment freely. By incubating a standalone AI concierge in the lighter-regulation U.S. market, Priceline can iterate quickly and quietly ship innovations that later flow upstream to its larger Dutch sibling.

Whatever the reason, Priceline is positioning itself as a quiet product lab for AI in travel. Worth watching, not because it’s flashy, but because they’re actually building something real.

For now, that’s it. Follow the job ads and you’ll spot travel’s next big bets months before the official announcement. Cruises, parks, hotels, OTAs – they’re all converging on one reality: AI talent is now the toughest first-class upgrade to snag on a transatlantic red-eye. Keep watching Skift AI Talent Tracker; the future of travel is being written one job requisition at a time.