AI Will Revolutionise How You Travel, Priceline CEO Says
By MICHAEL KAMINER
Tue, Jul 9, 2024 9:35am
4 min
4 min
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.
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Randy Boyagoda’s new novel, “Lords of Serendipity,” delivers a biting satire of cheating, politics and dysfunction across modern universities.
By
Thu, Sep 3, 2026 5 min
5 min
Administrative cowardice. Rampant cheating. The soaking and scamming of undergrads and grad students. Performative wokeism. Intensifying competition for international tuition dollars from an expansive China.
These are either the latest dire headlines about American higher ed or the myriad subplots of “Lords of Serendipity,” an ambitious new novel by Randy Boyagoda. Unlike most campus fiction, its scope extends well beyond the cloister of the liberal arts classroom to whammy the entire university system, from its financial model to its function within a globalized economy. Along the way, it skewers its lightning-rod targets with a precision too sharp to be considered entirely fictional.
That its author is not only well-versed in satire, having written four other novels in the genre, but is also a professor of English at the University of Toronto and an experienced college administrator, further blurs the lines between comic fiction and brutal fact. It’s the kind of no-holds-barred book only a consummate insider would know to write—but only one who is also conveniently outside the American university system could get away with writing.
“This is someone who’s got the inside dope on what can go on at universities, especially with international students, and what kind of con games are going on,” said Margaret Atwood, a friend and fellow Torontonian.
The novel, like Boyagoda himself, is often very funny—even as the dilemmas its characters face read as tragedy. Its cast includes the bickering members of a Sri Lankan hotel cleaner’s family, insecure American freshmen, dead-end third-tier college professors and their highflying Ivy League counterparts and dispirited university functionaries. An old-fashioned Dickensian tale, it sweeps across continents and campuses, from a classic liberal-arts college to a stand-in for Harvard University to an urban technical school to the dilapidated buildings of a state-run university in Sri Lanka.
“I’m a joyful person,” Boyagoda said in an interview, though he prefers to see his outlook on academia as “hopeful” rather than optimistic. He smiles and laughs frequently. He bikes everywhere. He derives energy from his students and from his four daughters, ages 14 to 20. They help him and his American wife, Anna, also an educator, care for Boyagoda’s father, an immigrant from Sri Lanka who has dementia and lives with the family.
The germ of the novel came to Boyagoda during the pandemic, when he was serving as a vice-dean. An urban legend was circulating about a statistics grad student selling passing grades to international students. The cheating scheme itself may well have been apocryphal, but it felt tantalizingly plausible.
“As a novelist, it stayed with me,” Boyagoda said. “Who would sell grades for a stats course? Why would someone buy grades? What’s motivating them? Why wouldn’t the university be doing something about it?” What he didn’t want to do, he explained, was write “another novel about a creative writing professor and his drama with students.”
In addition to writing novels—the first of which was a finalist for Canada’s prestigious Giller Prize; he’s written eight books in total—Boyagoda teaches literature full-time. For his students next semester, kids raised in a purportedly “post-literature era,” he’s assigning three 700-page novels, he noted mischievously, books by George Eliot, Ralph Ellison and Kiran Desai.
On RateMyProfessors, students remark on Boyagoda’s heavy assignments, tough grading and distaste for cellphones, but also hail his “comedy.” When alerted to these reviews, Boyagoda laughed. “Guilty as charged,” he said.
“Randy’s one of those people in academia who is very well educated but doesn’t have an ounce of superiority about him,” said John Irving, who frequently guest lectures in Boyagoda’s classroom. “It’s amazing to see how willing students are to talk in his classrooms, how little afraid they feel of being mocked or put down—he gets complete candor out of them.”
Negotiating competing interests seems to come naturally to him. Like many college campuses, after the Oct. 7 Hamas attack on Israel, the University of Toronto was embroiled in protests, encampments and discord; part of the school’s response was to convene a working group on civil discourse. Boyagoda was put in charge, serving for two years. It’s the kind of thankless task many professors would flee from, but Boyagoda relished the prospect and thinks the group, which is ongoing, made progress.
He has since pivoted to another formidable academic concern: the waning prestige of the humanities. In July, Boyagoda became the director of the Jackman Humanities Institute and special advisor on the humanities to the dean of arts and science. This fall, he is starting a series of gatherings he calls the Dead Book Club. (Dead writers feature heavily among his favorites: St. Augustine, Dante, William Faulkner, Evelyn Waugh, Saul Bellow.)
“The goal is to encourage students to read for its own sake and have conversation for its own sake,” Boyagoda said. “The importance of the humanities will be revealed to those who participate.”
“Lords of Serendipity,” which publishes next week, reflects Boyagoda’s commitment to the pursuit of knowledge: “I’m supposed to say I learn more from my students than they do from me, but no,” Boyagoda said. “I enjoy sharing my excitement and joy about literature and ideas. There are these moments when you are teaching and you can see someone’s face change because they didn’t know something and then they did. That moment when you’re actually watch someone enlarge themselves is deeply satisfying.”
In literary circles, Boyagoda is often referred to as a Catholic novelist, a description he embraces. “A novelist willing to give shape and voice to contemporary religious experience is needed,” Boyagoda said. “I understand myself as a Catholic novelist, provided that I’m not only a Catholic novelist, I’m also a South Asian novelist and I’m a Canadian novelist. I don’t want to be captive to one label.”
His characters, he said, are subjected to what he calls “Graham Greene character situations.”
“They are trying to do good in a fallen world and realize the most they can do is less harm than someone else would do in that same role,” he explained. “They have to accept they are complicit in something that provides some good thing to others. It’s a very Graham Greene way of thinking about sacrifice.”
The campus green they inhabit is a febrile zone in which lofty ideals and cynicism regularly collide. It’s a place where a traditional holiday college celebration is now an occasion for political protest. Kids freely police one another inside and out of the classroom with social media their constant, ready weapon of choice. International students, knowing their family’s financial futures hinge on their degrees, operate in terror of failure and deportation.
Early readers of the book include Gary Shteyngart and Junot Diaz, both of whom have taught at universities and written comic novels. They each contacted Boyagoda midway through to say, in essence, “You nailed it.”
As biting as “Lords of Serendipity” can be, Boyagoda’s faith in higher education remains undaunted.
“It’s absurd that we live in societies that make the decision to take people between the ages of 18 and 22, when they are most physically capable of contributing to our nations and communities, and tell them, ‘Go away for four years, and read and learn and have conversations,’” he said. “I want students to be aware of what an incredible privilege that is.”
Corrections & Amplifications
Randy Boyagoda is a special advisor on the humanities to the dean of arts and science at the University of Toronto. An earlier version of this article incorrectly said he is a special adviser to the dean of humanities. (Corrected on Sept. 2)
