Modern CTO The Business Strategy of the Biggest Player in Travel Tech with Rob Ransom, SVP at Booking Holdings
Jan 5, 2026
In this discussion, Rob Ransom, Senior Vice President at Booking Holdings, shares insights from the $100B travel empire behind popular brands like Booking.com and KAYAK. He reveals how AI is reshaping travel booking, likening its potential to that of mobile technology a decade ago. Rob highlights the importance of A/B testing in fostering innovation without politics, and emphasizes that simplicity drives effective business strategies. He also discusses the future of conversational booking and the incremental improvements philosophy that guides their approach.
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Hidden Portfolio Behind Famous Brands
- Booking Holdings is a holding company owning multiple well-known travel brands across categories and geographies.
- The public knows brands like Booking.com and OpenTable more than the holding company itself.
Joining To Integrate Acquired Startups
- Rob joined Booking.com in 2014 to integrate two acquired startups into hotel technology services.
- He led efforts offering websites, booking engines, and revenue tools for hotels.
Experimentation Culture Powers Decisions
- Booking.com built a rigorous A/B testing culture and centralized experiment tooling that drives product decisions.
- The experimentation approach lets ideas compete empirically and reduces political decision-making.