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This was the most useful, actionable advice we got on AI in 2025.
Today, we're compiling the best AI content we got from our Modern CTO of 2025: Rob Duffy, CTO at HealthEdge. We discuss why AI demos aren't translating to production ROI, how to treat AI migration with the same rigor as cloud migration, and why technical leaders must use AI tools themselves to drive organizational transformation.
All of this right here, right now, on the Modern CTO Podcast!
To learn more about HealthEdge, check out their website here.
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.
Peacock has become a streaming giant. How did they scale it to millions of users?
Today, we're talking to António Vieira, Director of Global Apps Engineering at Sky. We discuss how Peacock handles 30% of internet traffic during major NFL games, why live streaming is exponentially harder than video on demand, and how AI is being used to create personalized content experiences with synthetic voices.
All of this right here, right now, on the Modern CTO Podcast!
To learn more about Sky, check out their website here.
All tech is witchcraft…until it isn’t.
Today, we're talking to Sam Ransbotham, AI editor at MIT Sloan Management Review and host of the Me, Myself, and AI podcast. We discuss why 76% of executives now view AI as a coworker rather than a tool, how healthcare privacy laws from 1996 can't handle modern AI capabilities, and why cheaper coding will create more programming jobs instead of eliminating them.
All of this right here, right now, on the Modern CTO Podcast!
Thank you to Digital Ocean for sponsoring this episode. For simple cloud and powerful AI that’s built to scale, check out Digital Ocean here.
To read MIT Sloan's AI study, "The Emerging Agentic Enterprise," check it out here!
They’ve created a “Google Translate” for the cloud, and it’s changing everything.
Today, we're talking to Brad Parks, CloudOps and Private Cloud Leader at HPE. We discuss how Morpheus is bringing cloud operating models to on-premises infrastructure, why hybrid cloud is an inevitability rather than a strategy for most enterprises, and how HPE is helping IT teams eliminate vendor lock-in while maintaining workload portability across any infrastructure.
All of this right here, right now, on the Modern CTO Podcast!
To get learn more about HPE and Morpheus, check out their website here.
How is the biggest newspaper in the United States using GenAI?
Today, we're talking to Jason Sobel, CTO at The New York Times. We discuss how technology is transforming journalism for the digital age, why 70% of journalism jobs have disappeared in the last 25 years, and how The New York Times uses AI to enhance reporting without replacing human journalists.
All of this right here, right now, on the Modern CTO Podcast!
Thank you to Digital Ocean for sponsoring this episode. For simple cloud and powerful AI that’s built to scale, check out Digital Ocean here.
To get learn more about the New York Times, check out their website here.
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