Ex-CEO Brett Keller’s 26 Years at Priceline

When Brett Keller joined Priceline as marketing director in 1999, it was the third-largest U.S. online travel agency behind Travelocity and Expedia, and was selling Name Your Own Price airline tickets.

When Keller finished his 10-year run as CEO last month, Priceline was still selling flights — albeit in a more conventional fashion — and it offered 1.2 million accommodations in 166 countries as a brand within the world’s largest travel company, Booking Holdings.

In a recent Skift interview, Keller reflected on his tenure at Priceline, recalling how the company undercut Expedia by becoming the first OTA to eliminate flight booking fees and redefined brand marketing with the iconic Priceline Negotiator campaign with William Shatner.

He detailed how Priceline’s Penny chatbot has a dozen AI agents surrounding it, handling everything from shopping to cancellations. On the various LLMs’ agentic efforts, Keller said non-travel companies have never committed the necessary investments to adequately deal with the complexities of travel.

The proliferation of LLMs becomes a competitive advantage, according to Keller. “One of the things we love about this is it actually spreads out the competition at the top of the funnel,” he said. “It’s no longer Google only.”

The following is an edited Skift interview with Keller, who will stay on at Priceline in an advisory role until early April.

Skift: I remember when Priceline got rid of booking fees on airline tickets in 2007. That was such a big development.

Brett Keller: Yeah, that was a shocker. Expedia was making a fortune on airline ticket fees, and we were — and we were the number four OTA in the country, behind Travelocity and Orbitz and Expedia. And I remember talking about it with Jeff (then-CEO Jeffery Boyd). And basically the thought was, if we could eliminate booking fees on flights, financially it wouldn’t really hurt us that much, and it would kill them.

So we made the move to do that, and then we got a (William) Shatner campaign behind it. We created this character called “No Fee,” and he came in and we advertised with “No Fee crushes booking fees.”

That, with William Shatner, was just such a great campaign. That ad in particular worked so well. It literally almost tripled our flight business in a matter of a couple of months. It was so successful, and that really put us on a much faster trajectory to compete in the U.S.

Skift: Looking back at that, are there any lessons about fees today that are applicable to what you did back then?

Keller: More so than any other product, consumers are extremely sensitive to the price points around airline ticket fees, and so we made it a mission to save people money on airline tickets. So we’ve largely kept fees off of airline tickets, aside from where we provide real value and still save consumers money, such as with split tickets.

We have some fees that are applied to those because if they booked a round-trip flight with the same carrier, they’d end up paying more. So there’s value there for the consumer.

Skift: What about the broader proliferation of fees across travel — resort fees, bag fees, junk fees? It’s definitely a consumer pain point.

Keller: First of all, we live in the United States of America. A business has the right to charge any fee it wants on its goods and services. What’s not right is when it’s not fully disclosed.

Skift: You mentioned William Shatner. What’s your favorite William Shatner story?

Keller: The great thing about Bill is he was always 100% in on the operation with us. In particular, he was so passionate about the concept, about ensuring that he really represented who we are and what we did, and how we fought for consumers.

And so anytime we would launch a new campaign, we’d walk in and we’d show him the scripts, and he’d say, “these are great.”

And then he would give us, five or 10 new ideas on how he wanted to do it.

One time with Bill, and it was about three in the morning because we were trying to get so much done in a single shot. The director was a young guy, and he was just directing the talent in a very blunt and direct tone. He would tell Bill exactly how to say the words and exactly how he wanted it done. And Bill basically looked at the director and said, “I’m not a circus monkey. You can’t shove a quarter up my backside and expect me to spit out lines.”

He stood up, and left the set.

We had hundreds of thousands of dollars in this spot. So I go down and find him in the lobby. And he says, “Brett, I’ve been doing this for decades. This guy doesn’t know anything about acting.”

And he was right. Bill was such a pro. It took me about 10 minutes to finally convince him to finish the ad. He wanted the very best for Priceline. And so we love him; he’s been the best for us.

Skift: Priceline bought Booking.com, but I always felt Priceline should have remained the lead U.S. brand instead of Booking.com, which is based in Europe. What’s your take on it looking back?

Keller: I have a deep and abiding love for Priceline. It’s my home. We have always had very strong brand awareness in the United States, and we’ve been in a great position for years to compete very effectively here. Now with hindsight in place, I can legitimately say that we made the right decision as a group.

What Booking and Expedia both have are strong global businesses. Priceline does not have a global business. We have a very strong U.S. domestic business. In order to maximize all of the marketing channels in the U.S., you need to have a very strong inbound and outbound consumer flow.

Booking has that because of their strong presence in Europe and even more so in Asia. Now that allows you to invest significantly in performance channels. Priceline has never had the inbound flow, and without that, we lack the revenue to really compete at the very, very highest levels in the performance channels.

Skift: Let’s talk about AI. How is Penny doing, and where is generative AI heading for OTAs?

Keller: One of the benefits of being in the group (Booking Holdings), is each company gets to allocate their resources against technology and investment that makes sense for them. Because we’re smaller, we can move a lot faster than the biggest brands in the space, and that’s been true in AI. We jumped on it early.

We have a fully agentic model in place for Penny. So Penny operates as an agent that has multiple agents surrounding her that are doing independent workflows for her. And so now our whole company is building separate agents that all feed into Penny, and that’s going to be important for any brand to do longer term, meaning have the right architecture in place so that you can scale an agentic model to really do what we all want these models to do, which is to be a seamless travel concierge to plan, book and service you as a customer.

If you’re signed in on Penny, you just come in and you say, “Hey, I need to cancel my hotel.” Penny already knows, OK, Dennis has a booking at the XYZ Hotel. What Penny will do is immediately call a cancelation agent that our customer care technology team has built, and that agent does one thing and one thing only — it cancels hotel reservations.

Skift: How does this compare to what OpenAI and others are doing?

Keller: Priceline wasn’t the first connection (for OpenAI), but we’ve already built out our connection and will be part of that infrastructure, as well. We’ve seen this playbook multiple times because everyone wants to sell travel. Non-travel players do not invest enough resources to build out all of the complexities to sell and service travel.

They’ll never invest the resources to make that happen. Amazon has always wanted to sell travel. We went down this path with Google: First it was search, then it was their Hotel Ads business, and then it was Book on Google, and they dropped it. And now they’re talking about going back to it again. Tripadvisor had book on Tripadvisor, Kayak had book on Kayak, every one of them has [discontinued it].

One of the things we love about this is it actually spreads out the competition at the top of the funnel. It’s no longer Google only. It kind of spreads the consumers out a little bit more. We don’t have the risk of one single giant in the space eating up the entire funnel.

Skift: Looking back on your career, how do you see it?

Keller: I started in 1998 with Cendant and was working directly with AOL on their travel services, and then i joined Priceline in early 1999. It’s just been one of the most exciting rides I could have ever imagined. It’s the best industry to be in. I’ve never been bored for even a day in this industry, and so looking back, I just think I won the lotto when it comes to the industry.

Skift: What’s next? Are you going to sit back and play golf?

Keller: I’m 58. I retired for a specific reason. I was asked by our global church to serve as a mission leader with my wife. And so we are heading to Japan in July on a three-year assignment, based in Tokyo, and we’ll be overseeing close to 200 missionaries. They’re younger people, 18 to 22 years old. And I did the same thing when I was that age in Japan. I’ll come back. I can’t imagine not doing something, so I’ll probably get back into board work.

Get breaking travel news and exclusive hotel, airline, and tourism research and insights at Skift.com.