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How AI and advisors are humanising travel experiences: Matthew D. Upchurch, Virtuoso CEO

Last week, Virtuoso CEO Matthew D. Upchurch and Skift co-founder Rafat Ali took to the stage at the Skift Global Forum in New York to discuss the future of luxury travel advisors, the role of AI, and why personalisation and human connection have never been more vital in luxury travel. Karryon founder Matt Leedham reports from the Big Apple.

Last week, Virtuoso CEO Matthew D. Upchurch and Skift co-founder Rafat Ali took to the stage at the Skift Global Forum in New York to discuss the future of luxury travel advisors, the role of AI, and why personalisation and human connection have never been more vital in luxury travel. Karryon founder Matt Leedham reports from the Big Apple.

I’ve had the privilege of hearing Matthew D. Upchurch speak many times, and each time, his passion for the travel industry and visionary approach to the evolving role of travel advisors—especially in the luxury sector—never fails to impress.

Part presentation and part Q&A with Skift co-founder Rafat Ali, this session in New York titled ‘Humanising Travel in the Age of AI’ was no exception.

Speaking to a travel industry crowd of 1300 plus, Upchurch kicked off his time on stage by revealing that while as of this August, leisure travel worldwide had recovered 126 per cent of 2019 levels, his Virtuoso network is sitting pretty at 211 per cent, “which is absolutely amazing when you consider the growth in this industry,” he remarked.

Sharing his feelings on why this has happened, Upchurch said that for over twenty years, every industry has been polarised between being an optimised commodity and optimised experientially.

“If you want to personify this polarisation, you can think of two of the wealthiest people in the world, Jeff Bezos (founder of Amazon) and Bernard Arnault (founder of Moët Hennessy Louis Vuitton LVMH), as representatives of this polarisation. The danger is in the middle. You better be really good at one or the other. In my opinion, the number one protector of margin is how you made someone feel,” said Upchurch.

“At the end of the day, luxury is all about how you made someone feel—it doesn’t matter if it’s a tie, a scarf, or the way you interact with a human being in hospitality. That’s the number one protector.”

Matthew Upchurch, Virtuoso CEO at the Skift Global Forum. Image: Skift
Matthew D. Upchurch, Virtuoso CEO at the Skift Global Forum. Image: Skift

Clearly, Virtuoso continues to hit all the high notes in the feelings game. Touching on how technology is enabling the network’s luxury travel advisors to apply the human touch to excel even further, Upchurch explained, “Back in 2010 and 2011, we had two keynote speakers at our global conference who have become our North Stars: Simon Sinek, who wrote Start with Why (nobody knew him back then—he’s now been back four times), and Dr. Brené Brown, who also wasn’t widely known then but has since become an incredible thought leader.”

“Simon spoke about how people commoditise the “what” and buy the “why” behind something. Brené said that as technology becomes more ubiquitous, people will not only desire but crave authentic human connection. These two ideas validated our philosophy of automating the predictable so that you can humanise the exception. The rise of AI is allowing us as professionals to focus more on what it means to humanise the exception and go deeper into our value proposition.”

Highlighting, however, that sometimes, “the tech sector gets so enamoured with itself that it forgets simple things”, Upchurch was quick to remind the audience that “In 2007, mobility and social media fundamentally changed the profession of travel advisors. Travel advisors became some of the earliest, most successful digital nomads, and the role evolved from being a clerical desk job to an exciting, dynamic career.”

More younger people are using travel advisors than any other generation

Perhaps even more surprising (to some anyway) is the growing trend of younger generations recognising the value of travel advisors.

“Research from last year showed that Gen Zers are using travel advisors at a higher percentage than any other generation—utterly the opposite to what we were told to expect,” said Upchurch.

“In fact, I always credit the Millennials for bringing us back to the simplest definition of luxury: Of course, I can do it myself, but I don’t want to. Why would I if I have a professional collaborator who makes it fun, easy, and has my back?”

Talking about experiential travel, Upchurch said there’s one word he now uses for luxury travel: diversity.

“Luxury and experiential travel are incredibly diverse, and what’s exciting is that the diversity of our advisors matches the diversity of our clients. They can speak to them in their language and in the way they like to hear things. I’ve never seen advisors grow from zero to multi-million-dollar producers in such a short amount of time as I have recently in my 40-year career.”

Matthew Upchurch and Rafat Ali, Virtuoso CEO Skift Global Forum
Matthew D. Upchurch, Virtuoso CEO and Rafat Ali, co-founder of Skift, at the Skift Global Forum. Image: Skift

Transitioning into Upchurch’s 1-1 with Skift co-founder Rafat Ali, the Q&A began with Ali asking if Upchurch had used AI to plan his trips.

“Yes, and there are amazing use cases. One way our advisors are using AI is to help them think better and consider what they might be missing. Then they can build on that because it’s not just about the experience—it’s about who’s going to provide it.

“What’s really cool is that we have many different models within our network. We’re not trying to develop a single UX or follow one particular path. We have ex-Goldman Sachs professionals and super-mobile tech users, all using AI as an incredible productivity and thinking partner. We’re also developing our own models because, over ten years ago, I said we live in an era where answers are free. Being a “prompt engineer” is really about asking great questions. A lot of great advisors don’t impress sophisticated travellers with their answers, but with the questions they ask.”

One of the biggest skills of a great travel advisor is asking the right questions, right?

“100%. I always tell our advisors that if you say you’re in the business of booking travel, you’ve already lost before you’ve started. There are hundreds of thousands of ways to book travel. It’s the holistic value that advisors add before, during, and after the trip that makes the difference.

“For over 50 years, we’ve been studying what separates a trusted travel advisor from a transactional travel agent. The number one differentiator is some form of debriefing after the trip. This turns the relationship into a learning experience, where travellers can see how their trips improve over time.”

You’ve also added tech to this. What’s the state of travel advisor tech today?

“Back in 2014, everyone was talking about tech replacing travel agents. But there are two types of technology: one that removes as many people as possible and one that amplifies human connection.

“I’m happy to say that we’ve created a space for tech companies that understand the size and scope of the travel advisor business. I’m also excited about the new tech being developed. A lot of startups initially wanted to be B2C, but they ran out of money and pivoted too late to B2B. I’ve always said I don’t care if you’re B2C as long as you’re a good B2B partner. The best systems create a healthy tension between creative partners, making everyone more satisfactory through collaboration.”

You also work in the luxury world. What’s the state of luxury travel today?

“Our average ADR (Average Daily Rate) is US$1,000 per night, but the wealthiest customers don’t just drive luxury travel. It’s also aspirational. Many customers view it as an investment and want it managed by someone they trust. Some clients see us as the experienced version of a financial advisor, while others rely on us for specific, high-value trips.

“Right now, our sales are the strongest we’ve ever seen. If there’s a bubble, it will be bifurcated—those delivering real value will thrive, and those that aren’t will struggle. Employee culture is critical here. How a property’s staff makes you feel really matters, and that’s where the best luxury brands will continue to differentiate themselves.”

The commoditisation of big-box luxury. What’s your take on that?

“That’s a good question. I’ve realised that sometimes it’s not the brand but the ownership that matters. For example, the Fairmont Pacific Rim in Vancouver operates at an incredible level because the owner is personally passionate about maintaining standards. Some of our advisors are now booking hotels based on ownership, not just brand.”

We were also discussing the convergence of backpackers and luxury travellers. What’s your take?

“Today, luxury travellers and backpackers are closer than ever before. Luxury is no longer just about opulence; it’s about meaningful, experiential travel. Luxury travellers want to be participants, not spectators. They’re curious, they want to give back, and they seek authentic experiences. This evolution makes sense because many successful entrepreneurs today were once backpackers themselves 20-30 years ago.

“One of the reasons travel is booming right now is that we have six generations of people travelling simultaneously. Additionally, we’re seeing people prioritise spending on experiences over products. It’s a fascinating time for travel.”

That’s a powerful observation. What do you see as the next big trend in luxury travel?

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Matthew D. Upchurch, Virtuoso CEO and Rafat Ali, co-founder of Skift, at the Skift Global Forum. Image: Skift

“The next big trend is going to be deeper personalisation. We’re moving beyond just knowing someone’s preferences, like their favourite drink or room type. It’s about understanding what truly makes someone tick—what transforms their travel experience. Travellers want experiences that align with their values, like sustainability, wellness, or social impact. Personalisation will be about curating entire journeys that resonate emotionally. Technology, like AI, will help us deliver those experiences, but it’s the human touch that will elevate it.”

You mentioned sustainability—how do you see that evolving in luxury travel?

“Sustainability is absolutely critical, and travellers are demanding it more than ever. Luxury travellers, in particular, want to know if their travel is responsible. They’re looking for companies that align with their values, and they’re willing to pay a premium for that. This means more brands and travel advisors are integrating sustainability into their core offerings—whether that’s eco-friendly accommodations, carbon offset programs, or trips that give back to local communities. Sustainability isn’t just a trend anymore—it’s an expectation.”

It sounds like the future of luxury travel is very much about conscious, thoughtful experiences?

“Absolutely. Today’s luxury traveller wants to engage with the world responsibly. They want to explore, but they also want to leave a positive impact. That’s where our industry can really shine—by creating those connections between travellers and the world in a way that enriches both. It’s about making sure the experience is meaningful, sustainable, and aligned with the traveller’s values. And that’s what people are willing to invest in.”

The Skift Global Forum returned to New York City for its eleventh year and ran from 17 to 19 September 2024. Since its inception, the forum has been instrumental in shaping the future of the travel industry. In 2024, the global theme was Travel’s Great Renewal (and Reckoning), addressing the industry’s path forward amid economic uncertainties, political challenges, climate change, rapid technological shifts, and evolving traveller expectations. Matt Leedham attended as a guest of Skift.

For more details about the event, head to live.skift.com/skift-global-forum/