Kayak Co-Founders Launch Lola, Booking Holdings' AI Assistant
Steve Hafner and Paul English launch Lola, a new travel AI startup by Booking Holdings that replaces commissions with a membership model.
Stock photo for illustration only, not from the actual event
- Kayak co-founders Steve Hafner and Paul English launch new travel AI assistant Lola
- Lola operates as a wholly owned Booking Holdings startup built on a fresh tech stack
- Business model features free, $5/month Plus, and $25/month VIP membership tiers on 12-month commitments
- Team of roughly 20 employees split across New York and Cambridge after five months of development
Booking Holdings has introduced Lola, a new AI assistant designed to handle an entire trip from a vague idea to a completed booking within a single chat interface. Created by Kayak co-founders Steve Hafner and Paul English, the project was given a greenfield mandate by Booking Holdings CEO Glenn Fogel, allowing the team to build fresh code and branding from scratch.
The startup has been in development for five months and currently employs about 20 people divided between New York and Cambridge, Massachusetts. Operating as a wholly owned subsidiary of Booking Holdings, Hafner reports directly to Glenn Fogel while enjoying startup-style freedom backed by corporate resources.
Lola's monetization strategy replaces traditional OTA commissions with a membership model. The platform offers three tiers: free, a $5-a-month Plus tier, and a $25-a-month VIP tier, with both paid plans requiring 12-month commitments. This structure enables Lola to pass back the commission fees it would otherwise retain to the traveler.
According to company data, a sample four-night stay in Miami Beach costs $783 for a VIP member compared to $997 on Booking.com and Expedia. Supply extends beyond Booking Holdings brands to include OpenTable, ResX, SeatGeek, GetYourGuide, FareHarbor, BLADE, Aero, Nuitée, and Ten Group, with Ticketmaster, Live Nation, SevenRooms, and Resy currently under discussion.
"At Kayak, we were trying to solve what's the best flight. At Lola, we're trying to solve for what should I do this weekend."
Steve Hafner
Stock photo for illustration only, not from the actual event
Lola represents a bold strategic move by Booking Holdings to incubate a disruptive competitor from within, combining the agility of an early-stage startup with massive industry inventory. Shifting away from commission-based revenues toward recurring subscription models could redefine online travel economics and pressure major industry incumbents to rethink their user engagement strategies.
For human support, concierge firm Ten Group manages requests according to membership tiers, securing enhanced-benefit partnerships with roughly 5,500 to 6,000 hotels offering perks like room upgrades and late checkouts. Hafner projects that roughly 90% of active users will remain on the free tier, with the ultimate aspiration for Lola to achieve brand recognition on par with Booking.com.
Source: Skift
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