Modern CTO

Most people know booking.com. Almost nobody knows about the $100B+ travel empire behind it. Today, we're talking to Rob Ransom, Senior Vice President at Booking Holdings, about the business strategy behind booking.com, KAYAK, OpenTable, and more. We discuss how AI is transforming travel booking like mobile did a decade ago, why the best strategies prioritize simplicity over complexity, and how booking.com's legendary A/B testing culture removes politics from product decisions. All of this right here, right now, on the Modern CTO Podcast!  To learn more about Booking Holdings, check out their website here.

Today, we're doing something different: crowning the Modern CTO of 2025! In our first-ever year-end awards episode, we discuss the moments that stood out the most this year. From the most controversial moments to the wisest insights, we revisit the guests and clips that defined 2025 and reveal which tech leader earned the title of Modern CTO of the Year.

Shazam struggled to turn any profit for 6 straight years. But then the App Store changed everything. Today, we're talking to Chris Barton, Founder of Shazam. We discuss why they built a music recognition app eight years before the App Store launched, how they survived six consecutive years of near bankruptcy, and why eliminating the right friction is the key to massive user adoption. All of this right here, right now, on the Modern CTO Podcast!  To learn more about what Chris is up to, check out his website here.

Merry Christmas! Tune in next week to two of our favorite episodes of the year.

How did they reduce customer onboarding from 5 days to 7 minutes? Today, we're talking to Misha Keener, CTO at Flowable. We discuss why orchestration is more important than automation, how context engineering beats prompt engineering in agentic AI, and why enterprise readiness will separate winners from losers in 2025. All of this right here, right now, on the Modern CTO Podcast!  To learn more about Flowable, check out their website here.