Five Questions with Caitlin Austin, SVP of Marketing at Exclusive Resorts

Work & Co

In rapidly shifting to become a multi-brand luxury company, Exclusive Resorts feels almost like an LVMH, a luxury house of brands, but for travel. How do the recent acquisitions of Inspirato and onefinestay support your broader strategy and long-term aspirations?

Caitlin Austin

Under The Exclusive Collective, each brand plays a distinct role. Exclusive Resorts remains intentionally private—a true members-only Club built around a small, referral-based community. That privacy remains a defining strength, but it also means the Club is designed to serve a very specific audience.

Inspirato and onefinestay expand that ecosystem by serving as a new front door to our world. As our first true public-facing brands, they introduce us to luxury travelers we might never meet through the Club alone.

I think of it this way: Exclusive Resorts is a long-term, considered lifestyle decision, while onefinestay offers immediate access to a carefully curated collection of private homes, no membership required. Inspirato will add another dimension to the Collective, appealing to travelers who value flexibility through a premium, subscription-based model. Together, these brands give us the range to meet travelers earlier and stay with them as their needs evolve. One brand may offer the first stay; another may offer a lifetime of them—but all are designed to help people live richer, more intentional lives.

Work & Co

An early investor and someone instrumental in how we use the Internet today is Steve Case, your Chairman and majority owner. He often draws parallels between internet communities and the community of people that Exclusive Resorts brings together through travel. How do your digital experiences amplify members’ sense of community and what is the throughline with your resort experiences?

Caitlin Austin

The internet brought us closer together in a lot of ways (thanks Steve!), but it also taught us how easy it is to lose real community if everything stays online. That idea really shapes how we are continually innovating the Exclusive Resorts Member experience.

Our Members want more than a place to search and book, which is why we’re piloting a new digital “Clubhouse” in the Member Portal this month to help people connect over shared passions: skiing, food, wellness. We know our members find value in sharing the things they love — trading restaurant recommendations in Paris, talking about the best weeks in Telluride, or realizing a family they met in Anguilla will be in Jackson Hole the same weekend. One opportunity for us with digital is to spark those conversations early, so the real-world experience becomes even richer once they arrive.

The throughline to our resort experiences is this: we believe time is the ultimate luxury. Digital helps us protect it. AI can take the friction out of planning so our teams can focus on what actually requires judgment and care. At the same time, every Member is paired with an Ambassador who becomes almost like a personal trainer for the life you want to lead — someone who knows your preferences and your “no thank you” list.

That’s the balance we’re focused on. Some days you want the autonomy of planning yourself; other days you want someone to take the reins entirely. Tech handles the simple things. Humans handle the meaningful things. Personalization may start with data, but it becomes personal through people. Everything is designed to deepen the relationships members have with each other, not just with us.

Work & Co

In the age of AI and more screens than ever, you are offering IRL community building. What trends or insights are you seeing that reinforce the demand for in-person experiences over purchases?

Caitlin Austin

The clearest signal is our own growth. Exclusive Resorts has seen record-breaking demand over the past five years, which tells you where luxury travelers are headed: toward experiences that feel personal, culturally rich, and grounded in real community. There’s a real hunger for in-person connection. AI can make life faster, but it can’t replicate the feeling of being somewhere incredible with people who care about the same things you do.

Our Members are entrepreneurs, athletes, Fortune 500 CEOs — people who could easily let life be defined by achievement alone. Instead, many are united by something quieter: a determination not to live with regret. That sits at the heart of A Life Well-Lived, our podcast exploring the extraordinary people within our community.

This authenticity connects directly back to our investment in onefinestay. Our traveler community wants homes owned by architects, interior designers, filmmakers — people with real taste and a point of view. There’s also a generational shift as wealth transfers to Gen X and Millennials, who are prioritizing experiences over possessions. Instead of handing down a house no one uses, they’re handing down an Exclusive Resorts Membership — a commitment to time together.

So yes, AI will keep evolving. But the desire for real connection and community is only getting stronger, and that’s exactly where we’re focused: helping people experience the world in a way that actually matters.

Work & Co

One of the goals of your recent digital transformation was to accelerate the promise of luxury travel as early as trip research. To that end, how have you used customer insights to create a digital experience that meets luxury expectations?

Caitlin Austin

The biggest shift we’ve seen is that personalization is no longer a perk in luxury travel — it’s the baseline expectation. Our digital transformation started with listening to our Members, who told us they don’t want endless choice or complicated search paths. They want to feel understood from the first click.

Technology helps us do that efficiently. It gives us the intelligence to anticipate what someone might want based on how they travel, who they travel with, and the types of experiences they gravitate toward. If you’re a family of skiers traveling in March, for example, our platform surfaces the right homes with gear delivery and even a suggested grocery list in mind.

But the human layer is what makes it meaningful. Our Ambassadors use those same insights to curate options, refine recommendations, and guide Members in a way no algorithm ever could. The experience now feels more like being paired with a great concierge than dropped into a search engine — fewer but better choices, clearer storytelling, and a seamless handoff to a real person.

Work & Co

Do you have any predictions for how the travel booking experience will continue to evolve and adapt with AI?

Caitlin Austin

We’re moving toward an era where the browse-and-scroll model disappears. Instead of sifting through hundreds of options, you’ll simply say what you want and AI will surface the best choices instantly. The real unlock is personalization: using the data a brand already has about your preferences and past stays to build itineraries that feel truly tailored, so it becomes less about searching and more about being served.

But the bigger question is: served by whom? Trust is becoming the rarest commodity. Strong recommendations don’t come from scraped from the internet lists; they come from the lived experiences of 4,500 families who share your standards and your taste. The greatest luxury we can offer is confidence — knowing the suggestions you receive come from people you can trust.