This Week on Not Done: Chris Silcock, President of Hilton (drops tomorrow)
Chris gives a master class on leadership, generational shifts in hospitality, and why the next decade will reward the operators who move fastest.
4 Key Takeaways from Chris:
Great leadership = eliminating 40% of organizational BS through trust. When teams trust each other, velocity goes up dramatically.
LLMs will transform hotel search & booking. 58% of consumers already use ChatGPT-like tools for product recommendations, and Hilton is in deep engagement with the major AI platforms.
Brands are entering a generational moment of power. OTAs extracted billions over the last 20 years — but with loyalty, data, and scale, Hilton and peers finally have leverage to reset the economics.
Hilton’s massive partnership strategy is intentional. From Lyft to Amazon to SLH to AutoCamp — the goal is to offer experience-driven loyalty utility younger travelers actually want.
🔜 Next Week: Ben Rafter, CEO of Hotel Equities & Springboard Hospitality
Ben delivers a brutally honest look at operating complexity, AI adoption, culture integration, and why mid-scale/mid-size hotel companies are at a crossroads.
4 Key Takeaways from Ben:
The winners will be operators with real commercial engines. Revenue, content, marketing, and data science must be world-class — flags alone won’t save you.
Integration done wrong destroys owner relationships. Ben breaks down how they merged Springboard + HE without burying owners under bureaucracy.
AI is the new labor model. Larger platforms will use technology + regional specialization to extract 1% savings after 1% savings — because labor isn’t going down.
He’s still a startup guy at heart. Ben isn’t done — he literally says he’s “not done with one more startup or brand.”
This Week’s Power Moves in Hotels + Tech
1) Booking.com & OpenAI Team Up to Personalize Travel at Scale
Booking.com has rolled out multiple AI-powered features using OpenAI models to make trip planning more conversational and personalized — helping travelers move from “idea” to actual itineraries inside the Booking.com ecosystem.
Sloan’s Take:
OpenAI is no longer a toy in the browser; it’s in the pipes of the biggest travel platforms. If hotel companies aren’t building data + AI strategies with this reality in mind, they’re already behind. AI is and will be how most customers choose hotels now & in the future.
2) Anthropic’s Claude Targets Travel Personalization
Skift reports that Anthropic is working with travel brands to use Claude for hyper-personalized recommendations, customer support, and operational optimization, with a strong focus on safety and enterprise controls.
Sloan’s Take:
When both OpenAI and Anthropic are building for travel, that’s the signal: discovery, servicing, and ops will be run by AI agents. The “AI-native operator” is going to be a real competitive category.
3) Google’s AI Mode Now Visualizes Travel Plans in Search
Google’s new “Create with Canvas” inside AI Mode lets users design full itineraries — flights, hotels, activities — directly in search, with live pricing, Maps photos, and reviews. Draft trips are saved and can be iterated on with natural-language prompts.
Sloan’s Take:
Google is quietly becoming the world’s most powerful trip designer. Hotels that don’t build brand-level AI experiences will get relegated to line items in someone else’s canvas.
4) Booking.com Debuts Agentic AI Features for Guests & Partners
Source:
https://news.booking.com/bookingcom-debuts-agentic-ai-innovations-adding-to-its-robust-suite-of-genai-tools-for-customers/ Booking News
Booking.com launched Smart Messenger and Auto-Reply, agentic AI tools that help guests and accommodation partners handle questions and logistics automatically, and keep communication flowing without manual back-and-forth.
Sloan’s Take:
This is what real “AI in hospitality” looks like: not a gimmicky bot on a website, but embedded agents that reduce friction between guests and properties at scale.
Happy Holiday Season to all!
Not Done!
Cheers, Sloan