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Live webinar series

The Great AI Shake-up:
How hotel leaders should think about Agentic AI

Thursday 11 December 2025 10:30am EST | 3:30pm GMT | 4:30pm CET
 

AI agents are already recommending hotels to travelers and handling bookings. If you're a hotel leader trying to figure out what this actually means for your business, this session cuts through the noise.

Charlie Osmond (Triptease co-founder), Gilad Berenstein (built Utrip, the first AI trip planner), and Sanjay Vakil (DirectBooker) share what they've learned building and deploying AI in hospitality.

We'll cover:

  • How AI is changing distribution
  • Why most hotel AI projects fail and how to avoid the same mistakes
  • What "agentic AI" means for your revenue strategy
  • Your practical next steps

Join us for a straight talk about where AI is heading and what you need to do about it. This session is perfect for those who are AI-curious and those responsible for keeping their hotel competitive in an AI-first world.

You'll leave knowing exactly what to prioritize in your AI strategy and what to ignore.

Do you want to shape the content of the webinar? Submit your questions and challenges here, and we'll tackle them in upcoming sessions with Charlie and industry experts.

Speakers:

Charlie Osmond

Charlie Osmond

Chief Growth Officer
Triptease

Passionate about improving online travel, Charlie launched Triptease to help hotels deliver a better digital experience and increase direct bookings.

Charlie built his first business straight after graduating from Oxford with a degree in Engineering. He was named Young Entrepreneur of the Year by Esquire Magazine and one of HSMAI’s ‘Extraordinary Minds’. He won The Sunday Times £5M London Entrepreneur Challenge, is a Companion of CMI and a Fellow of the British American Project.

In his spare time, Charlie is a keen sailor and runner. His marathon exploits have taken him to Kazakhstan, North Korea, and Death Valley. In 2021, he set a World Record at the London Marathon dressed as Planet Earth.

Sanjay_Vakil

Sanjay Vakil

Co-Founder
DirectBooker

Sanjay Vakil is a seasoned product and engineering leader with a strong track record of driving innovation in travel, hospitality, and digital experiences. He spent the 90's at MIT training as an aerospace engineer culminating in a PhD – he's actually a rocket scientist.

Over the past two decades, he has played a pivotal role in shaping and shipping key products at industry giants like Google, Tripadvisor, and Time Out Group, with a focus on enhancing direct booking capabilities, optimizing digital advertising, and leveraging AI for personalization. During his tenure at Google, Sanjay led teams across Hotels, Flights, Things to Do, and Vacation Packages. For Hotels, he led projects like Free Booking Links, Official Site badging, AI-powered price retrieval, and building Extranet tools to improve supplier visibility and direct revenue.

With expertise spanning AI, metasearch, advertising technology, travel tech, and digital commerce, Sanjay continues to push the boundaries of how businesses engage with customers in an evolving digital world.

Sanjay is the Co-founder of DirectBooker, designing for the future of AI-driven distribution since its inception. They are taking their knowledge of planet-scale computing from Google and applying it to understanding how to capitalize on how AI is shifting the hotels ecosystem.

Gilad Berenstein

Gilad Berenstein

Founder
Brook Bay Capital LLC

Gilad is an Israeli born AI Entrepreneur, Board Director, and Venture Capital Investor based in Seattle. Gilad leads Brook Bay Capital, an AI focused fund, and serves on numerous boards of both large traditional businesses and startups, including Virtuoso, Faye, Mindtrip, and others. Gilad is passionate about Travel & Hospitality and related experiential and lifestyle businesses and has a deep background in Artificial Intelligence and Personalization. Gilad is eager to share his knowledge and in addition to his Board and Advisory roles Gilad is a friend and mentor to leaders across many of the largest consumer businesses in the travel, hospitality, retail, and related spaces, and to PE and other institutional investors in these industries.

Gilad has been on the forefront of AI and Innovation since he was a kid in the back of the living room listening to his dad who was an AI pioneer in the 1990’s. Today Gilad is one of the most prolific thinkers, speakers, and writers on the myriad of ways that AI, and what he coined as the Great Commoditization, are changing the ways we build and scale businesses, the ways we serve consumers, the realm of personalization and Dynamic Product creation, and the power dynamics at the core of our economy.

Gilad began his entrepreneurial career early founding his first startups in college. Most notably, Gilad was the founder and CEO at Utrip, a pioneering AI startup in the travel space founded in 2011. While at Utrip Gilad championed the utilization of AI and its integration, for the very first time, by many of the largest hospitality brands in the world. In addition to his investing and board work, Gilad is a prolific public speaker and speaks at many major industry and technology events.

Gilad is passionate about his young family, technology, travel, food, yoga, history, and the philosophy of AI.

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