Booking Holdings-backed Lola unveils membership model for AI travel and experiences assistant

Kayak co-founders Steve Hafner and Paul English have revealed new details about Lola, the Booking Holdings-backed artificial intelligence (AI) assistant they are building for travel, dining, events and other experiences.

The service will offer a free tier along with Plus and VIP memberships priced at $5 and $25 per month, respectively, with benefits including preferred hotel rates, dining access and travel perks.

Unlike Booking Holdings’ online travel brands such as Kayak, Booking.com, Priceline and Agoda, Lola will not accept advertising or paid placement, a distinction Hafner said is central to building trust in a personalized AI assistant. 

"Don't get me wrong, I used to love ads when I was at Kayak, but that's not the way we're running this program. We're designing a tool that our members want. You need to be able to trust the tool to not be influenced by third party payments, just purely by the member's preferences." Hafner told PhocusWire. 

"None of our partners can influence our search results, and that's really important to us because it's a membership model, which means we want to differentiate ourselves by giving you the very best personalized results that aren't influenced by commission payments or sponsorships, and our results don't have ads on it," Hafner said. 

The project first became public in May, and an initial Lola.com page went live. The new announcement details the membership plans, partners and booking capabilities. 

The brand name Lola dates back over a decade. English first founded the Boston-based startup in 2015, with aspirations of building a consumer-facing app that would act as a travel concierge. 

The app relaunched in 2017, pivoting to focus on business travel and partnering with American Express Global Business Travel the following year. In 2021, Lola shut down its services, citing "new things to come" for the company on its website.  

"We've basically been building an AI assistant for all things worth doing, so travel, dining events, you name it, we're going to do it," said Hafner, who stepped down from his role as Kayak CEO in February. At the time, the company said Hafner would step into a new, AI-focused leadership role at Booking.

Rather than focusing on broader travel, Lola zooms in on experiences.

"We've got plenty of travel agencies within the group. We're not trying to be your travel agent. We're actually trying to be your agent for anything that's worth doing," Hafner said. 

Lola's launch partners include travel players such as GetYourGuide, Nuitée and Aero, as well as Booking Holding brands such as Booking.com, Kayak, Priceline, Agoda, FareHarbor and OpenTable.

The 20-person Lola team is based in New York and Cambridge, Massachusetts—a team Hafner said would likely have been much bigger before the age of AI.

Access to Booking's APIs acts as a "force magnifier" for Lola's small team, according to Hafner.

"With those 20 people, you can get way more done today than you could even last year. Our advantage versus other companies is our innovation velocity."

Booking Holdings CEO Glenn Fogel and CFO Ewout Steenbergen have previously mentioned plans for AI startups on the East and West Coast, with Lola now filling the East Coast slot.

Hafner declined to comment on the status of the West Coast startup.

Membership model

Hafner noted that the membership component means you can't use Lola anonymously, unlike other travel and experience sites. And that's intentional.

"We want to personalize the experience, so we need to know who you are. That way, we connect the dots for how you've interacted with Lola in the past. You don't always have to tell us what you like. We just learn what you like."

The paid tiers offer added perks and benefits via Lola's partner network, and both Lola Plus and VIP memberships have a 12-month commitment.

Plus members access preferred hotel rates through Booking.com, Priceline, Agoda and Nuitée, saving 10%, while VIPs save up to 15% on four- and five-star hotels. Both tiers also receive travel-related discounts on GetYourGuide activities and their first Aero flight.

"By having a membership model, if you join one of our two paid offerings, we pass all these discount and perks back to you," Hafner told PhocusWire.

When asked who pays for the discounts offered, Hafner said both Lola and its partners account for a portion.

"It's not too dissimilar from what the premium credit card programs are doing, but this is a lower entry point, and you can do Lola without having a particular card," Hafner said.

When a user decides to book, they can stay on Lola or leave. If they stay within the chat, payment is handled via Lola's APIs.

The roadmap

Within the competitive space, Hafner said Lola is relying on the strength of its product and stands out from other large language models thanks to its vertical, focused approach.

"Instead of trying to access publicly available rates via browser extensions or without explicit permission, we have partnerships with the branch whose inventory we're bringing in," he said.

"Everything is via APIs, it's in real time, these are live prices. Not only do we want to make great recommendations, but we want you to get a transaction out of it if you want to."

To attract users, Hafner described a three-pronged approach: offering a solid product, influencer marketing and word of mouth and virality.

"We only want to acquire you once. That's why influencer marketing works. We're not going to do Google paid search. You're not going to see us on billboards or on TV. We'd like you to use our product, earn your loyalty so that you always use us for your travel and your events and experiences."

Hafner said the focus is on "making Lola the destination," encouraging users to choose the platform over other newcomers such like Meta's Muse.

"It's the execution that really matters. The big folks have a data advantage for breadth across verticals, but they don't have it within depth," he said.

"When I play around with [Muse] and I try to book a table or book a hotel, it can't do it, and where it can do it, I'm not getting the best price or it's too slow, etc. So that's what we're trying to solve."

There are also several plans for Lola, including the ability to link a Google account and book flights.

"Lots of other brands are doing that right now—I don't know that they're doing it well," Hafner said of flight booking capabilities. "Kayak did it, I thought, pretty well, but it's not bookable on Kayak. So, we want to solve flights too. It's just there's other stuff we want to get to first."

An agentic component is another possibility.

"At some point, we'll get to be agentic," Hafner said. "The agentic component for us right now is turning a recommendation into a reservation. Someday we'll move on to anticipating changes in prices or changes in availability or cancel, rebook, that kind of stuff, but right now, recommendations becoming reservations—if we get that right, we're in good shape."