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.

Luke Michel has already lived through two technology overhauls in his career, first desktop publishing in the 1980s and online publishing later on. But AI? He’s had enough.

So when his employer, the Dana-Farber Cancer Institute, made an early-retirement offer to some staff last year, the 68-year-old content strategist decided to speed up his exit. Before, he had expected to work a couple more years.

“The time and energy you have to devote to learning a whole new vocabulary and a whole new skill set, it wasn’t worth it,” he said.

It isn’t that he’s shunning artificial intelligence—he is learning Spanish with the help of Anthropic’s Claude. But, at this point, he’s less than eager to endure all the ways the technology promises to upend work.

“I just want to use it for my own purposes and not someone else’s,” he said.

After rising for decades and then hovering around 40% in the 2010s, the share of Americans over 55 years old in the workforce has slipped to 37.2%, the lowest level in more than 20 years.

The financial cushion of rising home equity and stock-market returns is driving some of the decline, economists and retirement advisers say.

But for some older professionals, money is only part of the equation.

They say they don’t want to spend the last years of their career going through the tumult of AI adoption, which has brought new tools, new expectations and a lot of uncertainty.

Many people retire when key elements of their work lives are disrupted at once, said Robert Laura , co-founder of the Retirement Coaches Association and an expert on the psychology of retirement.

“Maybe their autonomy is being challenged or changed, their friends are leaving the workplace, or they disagree with the company’s direction,” he said.

“When two or three of these things show up, that’s when people start to opt out.”

“AI is a big one,” he adds. “It disrupts their autonomy, their professionalism.”

Michel, whose work required overseeing and strategizing on website content, has been here before.

When desktop publishing arrived in the 1980s, he was a graphic designer using triangles and rubber cement.

The internet’s arrival changed everything again. Both developments required new skills, and he was energized by the challenge of learning alongside colleagues and peers.

It felt different this time around. “Your battery doesn’t hold a charge as long as it used to,” he said.

He would rather spend his energy volunteering, making art, going to operas and chairing the Council on Aging in North Andover, Mass., where he lives.

In an AARP survey last summer of 5,000 people 50 and over, 25% of those who planned to retire sooner than expected counted work stress and burnout as factors.

About half of those retired said they had left work at least partly because they had the financial security to do so.

In general, older Americans are less likely than younger counterparts to use AI, research shows.

About 30% of people from ages 30 to 49 said they used ChatGPT on the job, nearly double the share of those 50 and older, according to a 2025 Pew Research Center survey of more than 5,000 adults.

Baby boomers and members of Generation X also experienced the sharpest declines in confidence using AI technology, according to a ManpowerGroup survey of more than 13,900 workers in 19 countries.

“We as employers aren’t doing a good enough job saying (to older workers), we value the skills that you already have, so much so that we want to invest in you to help you do your job better,” says Becky Frankiewicz , ManpowerGroup’s chief strategy officer.

Jennifer Kerns’s misgivings about AI contributed to her departure last month from GitHub, where the 60-year-old worked as a program manager.

Coming from a family of artists, she said, it offends her that AI models train on the creative work of people who aren’t compensated for their intellectual property. And she worries about AI’s effect on people’s critical-thinking skills.

So she was dismayed when GitHub, a Microsoft-owned hosting service for software projects, began investing heavily in AI products and expecting employees to incorporate AI into much of their work. In employee-engagement surveys, the company had begun asking them to rate their AI usage on a scale of 1 to 5.

When it came time to write reports and reviews, colleagues would suggest that she use ChatGPT.

“I’d be like, ‘I have no idea how to use that and I have no interest in using AI to write anything for me,’” she said.

It would have been more prudent to work until she was closer to Medicare eligibility, she said. But by waiting until her children were out of college and some of her stock grants had vested, the math worked.

Her first act as a nonworking person: a solo trip to Scotland, where she took a darning workshop and learned how to repair sweaters.

“The opposite of AI,” she said.

Employers already under pressure to cut workers—such as in the tech industry—may welcome some of these retirements, said Gad Levanon , chief economist at Burning Glass Institute, which studies labor-market data.

“The more people retire, the fewer they have to let go,” he said.

Some of the savviest tech users are also balking at sticking around for the AI upheaval. Terry Grimm, who worked in IT for 40 years, retired from his senior software consultant role at 65 last May.

His firm had just been acquired by a bigger firm, which meant learning and integrating the parent company’s AI and other tech tools into his work.

Until then, Grimm expected he might work a couple more years, though he felt that he probably had enough saved to retire.

“I just got to the point where I was spending 40 hours at work and then 20 hours training and studying,” said Grimm, who has since moved with his wife from the Dallas area to a housing development on a golf course in El Dorado, Ark.

“I’m like, ‘I’ll let the younger guys do this.’”

AI Will Revolutionise How You Travel, Priceline CEO Says

Their careers spanned the personal computing, internet and smartphone waves. But some older workers see AI’s arrival as the cue to exit.