Smarter Reservations: AI, Customer Experience, and Dylan Ratigan’s Master Plan

In a crowded travel-tech space, Ratigan bets on artificial intelligence and high-touch service to reshape how we book the moments that matter.
When Dylan Ratigan acquired Reservations.com, it wasn’t just a strategic purchase of a high-impact domain – it was the foundation of a broader vision: to build a unified, intelligent, and customer-first platform capable of reshaping how people book everything from hotel rooms and fine dining to theatre tickets and spa appointments. Drawing on his background in media, finance, and systems thinking, Ratigan is leading an ambitious project that fuses technology, service, and scale. In this exclusive conversation, he outlines how Reservations.com is being reimagined to meet the evolving demands of modern consumers – and why he believes the timing is perfect.

What motivated you to acquire Reservations.com, and why now?

The domain itself holds immense strategic value. Reservations.com isn’t just a name-it’s a universal call to action. It signals trust, utility, and immediacy. The opportunity lies in the sheer scope of what this domain can encompass-not just travel, but restaurants, cultural events, wellness bookings, and more. It’s a digital front door to an entire ecosystem of services that rely on reservations. In a world increasingly defined by convenience and immediacy, owning this kind of access point positions us perfectly for scale.

How would you define the long-term vision for the platform?

The core ambition is to build a single, intelligent platform that enables users to book anything requiring a reservation-quickly, seamlessly, and with confidence. Whether it’s securing a hotel room or grabbing a last-minute table at a top-tier restaurant, the experience should feel unified and effortless.
But more than that, I want to redefine what service feels like in the booking space. I spend about a third of my life traveling. That gives me a firsthand understanding of what world-class service really looks like-and how rare it is. My vision is to bring that level of care and attention to everyone, not just VIPs. Customer experience will be the cornerstone of everything we build.

You’ve mentioned AI as a central pillar. How exactly will that be integrated?

AI is going to be transformative-not just as a back-end tool, but as a real-time guide for users. We’re working on systems that can detect intent, streamline the search process, and deliver hyper-relevant options instantly. Instead of clicking through dozens of tabs, users will get precisely what they need-fast.
Think of it this way: the ultra-wealthy have personal assistants who manage their bookings. What if we could provide that same level of curated, responsive service-at scale-for everyone? AI allows us to do that. And the technology is advancing fast enough now to make it not just possible, but inevitable.

Who are your key collaborators in this venture?

I’m fortunate to be working alongside some of the most experienced figures in the travel and hospitality industry. HotelPlanner, in particular, brings exceptional knowledge and infrastructure to the table-especially in the area of group bookings and specialized hotel inventory. We’re not starting from scratch; we’re building on a foundation that already works, and enhancing it with next-generation tools and user experiences.

What’s the business model, and how do you plan to compete in a saturated marketplace?

Our model prioritizes customer retention and trust over short-term clicks. That means focusing on value: better inventory, better prices-often via closed user group deals-and a more intelligent user experience. We’re not trying to outbid others in the race for Google Ads. We’re investing in building a loyal user base that comes to Reservations.com because it simply works better.
The long game is all about delivering consistent, high-quality experiences that keep people coming back-and telling others.

Why begin your rollout in Europe rather than the U.S.?

Europe is a complex, diverse, and demanding market, which makes it an ideal testbed. It’s culturally rich, linguistically fragmented, and full of regulatory variation-exactly the kind of environment that stress-tests both tech and service models. I live in Italy, so I also have a close-up view of how different the expectations can be from city to city.
If we can get it right in Europe, we’ll be in a very strong position to scale in the U.S., where the infrastructure is more uniform but the competition is steeper.

Looking ahead, what excites you most about this venture?

The chance to fundamentally change how people engage with the world. Booking isn’t just a transaction-it’s a moment of intention, a step toward a desired experience. If we can make that process smarter, faster, and more human, we’re not just building a platform-we’re enhancing the way people live. That’s the mission. And we’re just getting started.

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