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The Great AI Shake-Up: Webinar Series

Next session: Thursday 11 December 2025 10:30am EST | 3:30pm GMT | 4:30pm CET
 
The Great AI Shake-Up is a monthly live event series exploring how artificial intelligence is reshaping the world of hotel marketing. Hosted by Charlie Osmond, Triptease Co-Founder, each session brings together hospitality innovators, data experts, and AI leaders to uncover the tools and strategies redefining how hotels attract, convert, and retain guests. From smarter pricing to hyper-personalized experiences, the AI Series helps hoteliers navigate the opportunities — and challenges — of intelligent hospitality. 

More than a webinar, The Great AI Shake-Up is a space for forward-thinking hoteliers to learn, exchange ideas, and stay ahead of the curve. Through real examples, live discussions, and expert insights, each session reveals how AI can drive direct bookings, unlock efficiencies, and enhance every step of the guest journey. Whether you join live or on demand, you’ll gain the clarity and inspiration to put AI to work in your hotel strategy today.

You set the agenda. Submit your questions and challenges here, and we'll tackle them in upcoming sessions with Charlie and industry experts.

What you'll learn

Explore how artificial intelligence is transforming hotel marketing — from strategy to guest experience.

Each live session of The Great AI Shake-Up reveals practical insights, tools, and real-world applications designed to help you stay competitive in the age of intelligent hospitality.

You’ll learn how to:

  • Apply AI to drive more direct bookings and improve conversion.
  • Use real guest data to personalize every stage of the journey.
  • Automate content and communication for greater efficiency and engagement.
  • Leverage predictive analytics to anticipate demand and optimize pricing.
  • Discover how leading hotels are already using AI to outperform OTAs and delight guests.
  • Come for the insights — stay for the ideas that will transform your approach to hotel marketing.

Host:

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.

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