The KAYAK founders are back with an AI assistant for the hours between trips. Inside Booking Holdings, Lola pairs conversational planning with member rates and a human who knows whom to call.
It started with two hotel websites and a tropical hunch that Asia would book its next holiday on a phone. Two decades later, Agoda runs one of the planet's busiest travel marketplaces - and quietly powers the trips you book somewhere else.
Ted Clements is the CEO of WeTravel, a San Francisco-based payments and booking platform for multi-day and group travel operators. He took the top job in January 2023 after co-founder Johannes Koeppel stepped aside to become Chief Product Officer and personally recruited him. Clements built his career at FareHarbor, joining as one of the first mainland US sales reps and rising to COO and acting CEO, helping scale the day-tour software company to 700-plus employees and an acquisition by Booking Holdings. In September 2025 he led WeTravel through a $92 million Series C round from Sapphire Ventures, pushing the company toward its goal of becoming the operating system for the fragmented multi-day travel market.

Pierre-Olivier Lepage is the CEO and co-founder of Cruisebound, a New York-based digital-first cruise booking platform he launched in 2022 after struggling to book his own first cruise online. A Polytechnique Montréal engineering graduate who earned dual MIT master's degrees in Transportation and Operations Research, Lepage previously built operations at Rocket Travel (a Booking Holdings company) and consulted at McKinsey before betting that the $66B cruise industry — where 80% of bookings still flow through travel agents — was ripe for a tech-native overhaul. Cruisebound has since raised $37.8M in total funding, serves customers averaging nine years younger than typical cruisers, and routes 42% of support queries through AI, positioning itself as the fastest-growing national online cruise agency.
OpenTable is the online restaurant-reservation marketplace that connects diners with tables and gives restaurants the software to manage them. Founded in San Francisco in 1998, it pairs a consumer booking app and website with a back-of-house table-management and CRM platform, helping more than 60,000 restaurants worldwide seat roughly 1.9 billion diners a year. It is owned by Booking Holdings, which acquired it in 2014 for $2.6 billion.
Debby Soo is the CEO of OpenTable, the global restaurant reservation platform serving 65,000+ restaurant partners across 110+ countries. A Stanford and MIT Sloan alumna, she took the helm in August 2020 — at the precise moment the pandemic shuttered restaurants worldwide — and transformed the business by shifting its focus from diners to restaurants as the primary customer. Under her leadership, OpenTable has achieved double-digit revenue growth in 2025 and quadrupled its share price since she joined, while forging strategic partnerships with Visa, JPMorgan Chase, and OpenAI.