AI Will Revolutionise How You Travel, Priceline CEO Says

With its 1997 launch as a name-your-own-price site, Priceline helped usher in the era of online travel booking―and the growth of a trillion-dollar category. Priceline itself has mushroomed into a global business with 1,500 full-time employees; along with global airline bookings, the site claims to offer 1.2 million accommodations in 116 countries.

Now, the Connecticut-based company is focusing on generative AI, and CEO Brett Keller is behind the leap. It’s just the latest technology push from Keller, a 25-year veteran of the company who has also served as CMO and COO. Under Keller, Priceline launched the travel industry’s first full-service mobile app in 2009; he also helped conceive the hugely popular William Shatner-fronted “Negotiator” ad campaign.

Keller, 56, talked to Penta about how AI is changing travel planning, what luxury travellers do to save money, and why Japan blows his mind.

Penta: Much of Priceline’s marketing is about value. Do you see luxury travellers in your customer mix along with budget-conscious travellers?

Brett Keller: High-net-worth consumers take a significantly higher number of trips than the average leisure traveller. For a high-end vacation like a safari in Tanzania, they’ll work with experts. But for the other 30 trips they book that year, either for themselves or family members, they don’t always reach for the stars. They want to manage money effectively. And as they’re moving around the country and the world, they need a fast, easy way to book travel that accommodates their needs. Priceline is a great platform for that kind of trip. And if you’re taking a quick weekend trip to Miami, and want to stay in the Four Seasons, we’ve negotiated with them. Even high-net-worth individuals seek value.

Priceline made headlines last year for partnering with both Google and OpenAI on Penny, your AI assistant. How has Penny evolved?

She’s gone from, “I can answer questions about the hotel you’re looking at” to actually servicing the customer through more complicated scenarios. If you need to cancel a hotel that’s fully refundable, you can do it with one click. But if there are issues, like a reservation that’s not fully cancelable, Penny can walk through those steps for you.

Penny’s also helping people find, search, and book properties. For example, if the customer tells her, “I’m looking for a great resort with these features, anywhere warm”—she’ll present recommended properties that meet those requirements. You can continue with Penny on the site, or go with the traditional experience.

Has there been any pushback from consumers about Penny and generative AI?

There has been none. Customers still have access to phone agents. Anyway, the younger generation doesn’t want to talk to anyone. And with traditional chat agents, live agents, or even messaging apps, there’s typically a delay. Penny answers immediately and in real time.

What’s the future of generative AI and online travel booking?

The future is a highly personalised shopping experience. It’s hard to achieve, because we don’t know about the consumer when they come in. But generative AI lets us dramatically improve personalisation. As you work with Penny, and tell us your preferences, the way you interact lets us find and book the best products and services every time you return. The ability to customise and personalise increases exponentially.

Is the travel experience even more bifurcated between elite, ultra-high-net-worth travellers and everyone else?

Consumers seem to be a little less sensitive in some areas. On planes, first-class and comfort-plus seats are the first to go, most of the time, and people are burning through points to sit in the front because they’re tired of not having legroom. But seats are packed in economy, too, so people are flying.

Hotel bookings are more economically driven in the U.S. Higher-income people are not as affected by interest rates or the cost of living, so they spend more freely than economy-minded consumers. There is a bit of bifurcation there. The low end is not filling, but the high end is.

It’s been reported Europe’s going to get even more crowded this summer. Does Priceline ever suggest alternatives to over-touristed or overpriced destinations?

We’re not in the business of telling you where you shouldn’t travel. We market popular destinations because that’s where people want to go. As much as we could tell people, “Las Vegas is overcrowded, don’t go,” people will want to go.

Social media is highlighting some overpopulated destinations and suggesting alternatives, so that comes back to us. But price is the No. 1 motivator. Vegas is a great value. There are so many hotel rooms available that you can go in a non-peak period and get a room in a four-star hotel for US$120. Try doing that in New York City.

What destinations are going to pop over the next year or two?

Asia will continue to be exciting and interesting to people. Bangkok is a great place to move in, then travel throughout Southeast Asia. As the region gets more popular, people will keep trying to find more remote and more unique destinations. People love Europe, but it was the hot spot in 2022 and ’23. Some travellers are saying, “I’ve had enough, and I’m moving on.” Japan is also amazing, for so many reasons. It’s easy to navigate. English is not a challenge. It’s safe. It feels like a different world, but completely first-world. The strength of the dollar is also driving some of that―again, price plays a role.

Beyond that, Mexico and the Caribbean took a real hit in 2022 and ’23 after a boom in 2021. They’re coming back now. A lot of people don’t want to travel far—“I just want to go to a beach and not think of anything.” And because not everyone wants to travel overseas, unique and relaxing cities like Nashville, Tennessee; Houston; and Austin, Texas, will be popular, especially into the fall.

Every day brings more headlines about airline woes. Who gets blamed if a Priceline customer has a bad flying experience, you or the airline?

When you have a bad experience traveling, you want to blame everybody. No matter what happened, the online travel agency takes blame and the airline takes the blame. It could be your seat, the person sitting next to you, whatever. We get the complaint, and we take on that responsibility and that role. We have leverage because of the amount of business we drive to partners. They want to work with us to make sure the customer has the best experience. Something goes wrong almost every time you take a trip. That’s just the reality.

What are your favourite places to travel?

My favourite destination, and a place where I spend a lot of time every summer, is [resort town] McCall, Idaho, one of the most beautiful towns in the West, with hiking, trails, and mountain biking. Outside of the country, it’s Japan, absolutely. Tokyo is the most exciting city in the world. It’s mind-blowing.

This interview has been edited for length and clarity.

Australian football superstar and Matildas captain Sam Kerr has joined one of the world’s most exclusive luxury watch brands, reflecting on the sacrifices behind a career at the pinnacle of professional sport and revealing she only signed with her new club last week.

As Richard Mille’s first and only Australian partner, Kerr has joined an elite group of global athletes, artists and innovators associated with one of the world’s most prestigious watchmakers.

Speaking in Sydney, the 32-year-old reflected on her next chapter, the extraordinary growth of women’s football and the personal sacrifices required to reach the top of the game.

Founded in 2001, Richard Mille has built a reputation for producing some of the world’s most technically advanced and exclusive timepieces. The Swiss watchmaker is renowned for its use of ultra-lightweight materials, Formula One-inspired engineering and limited-production watches that often sell for hundreds of thousands of dollars and, in some cases, more than $1 million.

Its ambassadors include tennis great Rafael Nadal, Formula One stars Charles Leclerc and Lando Norris, actress Michelle Yeoh and sprint champion Shelly-Ann Fraser-Pryce.

During the Sydney event, Kerr wore the Richard Mille RM 07-04 Automatic Sport, a lightweight model featuring a pink case, blue strap and skeletonised movement. Designed for active lifestyles, the watch reflects the brand’s philosophy of combining high-performance engineering with luxury craftsmanship.

For Kerr, becoming the brand’s first Australian partner is a source of considerable pride.

“Of course, being the only Australian is incredible to me,” she said. “I am very proud to be Australian and I like to put Australia on the map.”

The announcement comes as Kerr prepares for the next stage of her football career following her departure from Chelsea after six-and-a-half years.

While speculation around her future has been mounting for months, Kerr revealed a decision was only finalised recently.

“Everyone thinks that it was decided and I’ve known that (it was) reported that I’d signed somewhere in April, but honestly, I only signed my contract on Wednesday last week,” she said.

“I really hadn’t decided what I was going to do until last week.”

Kerr said she expects details of her new club to be announced around the beginning of July once her Chelsea contract officially concludes.

Despite her excitement about what lies ahead, she admitted leaving one of the world’s biggest football clubs has been emotional.

“I am really sad about it,” she said. “It’s been my home for 6.5 years. I have so many good memories there. I have so many amazing teammates. I’m sad to leave.

“It sucks to leave such a big club like Chelsea too, but it comes to an end to everything, right?”

The 32-year-old also reflected on the transformation of women’s football during her career, describing the Matildas’ rise from relative obscurity to household-name status as one of her proudest achievements.

“What the Matildas have done over the last four or five years has been incredible,” she said.

“The most important thing for me is that you leave the game in a better place.”

Kerr noted that when she began playing, there were few professional pathways for women, limited sponsorship opportunities and crowds that bore little resemblance to those regularly attending matches today.

“We are a part of that generation that still knows what it was like when there was no one in the crowd,” she said.

Today, she said, crowds of tens of thousands remain something the team never takes for granted.

“Even last night we had 20,000 on a Tuesday night nearly. That’s special to us,” she said.

“We feel very lucky that people come out and spend their money and come to a game and watch us.”

Yet behind the accolades, sponsorships and sold-out stadiums, Kerr said there have been significant personal sacrifices.

“I’ve been living out of home since I was 17 years old. I’ve missed a lot of my family’s life,” she said.

“I’ve missed a lot of weddings. I’ve missed funerals. I’ve missed so many things that people don’t see.”

Kerr revealed she was unable to return home for her grandmother’s funeral last year because of football commitments.

“You have to love what you’re doing. You have to want to sacrifice,” she said.

“Everyone makes sacrifices, of course, and what I do is a massive privilege, but there comes a lot of sacrifice with it.”

Away from football, Kerr said Australia remains central to her identity despite spending much of her adult life overseas.

“I think we take for granted in Australia the beaches, the ocean, the open spaces,” she said.

As she prepares for a new club, a new season and a new role with Richard Mille, Kerr said she remains motivated by the same passion that first drew her to the game as a teenager.

“It was really organic,” she said of her relationship with the luxury watchmaker.

“It’s a real family brand.”

AI Will Revolutionise How You Travel, Priceline CEO Says

The Matildas captain has joined one of the world’s most exclusive luxury watch brands, sharing candid insights into the sacrifices required to succeed at the highest level of world football.