Modern CTO

How should you respond to the fastest shift in tech we've ever seen? Make more mistakes.

Today, we're talking to Andrea Iorio, author of Between You and AI and former Chief Digital Officer at L'Oréal. We discuss why asking better questions matters more than having all the answers, how reverse mentoring can transform organizational learning, and why becoming antifragile through smart mistakes is the key to thriving alongside AI.

All of this right here, right now, on the Modern CTO Podcast! 

To pick up a copy of "Between You and AI," check it out here!

THIS is how you keep your infrastructure costs from spiraling out of control.

Today, we're talking to Albert Strasheim, CTO at Rippling. We discuss the cost crisis facing CTOs in the age of AI, how he reduced infrastructure costs by 30% while growing traffic by 25%, and why holding back feedback is actually the most selfish thing a leader can do.

All of this right here, right now, on the Modern CTO Podcast! 

To learn more about Rippling, check out their website here.

Has AI really become THIS powerful in the enterprise?

Today, we're talking to Brian Elliott, CEO at Blitzy and Tom Jackson, CTO at RSM US LLP. We discuss how AI agents are autonomously completing months of development work in days, why organizational change management is now the biggest bottleneck in software development, and how enterprises are achieving 5x engineering velocity with agentic SDLC platforms.

All of this right here, right now, on the Modern CTO Podcast! 

To learn more about Blitzy, check out their website here.

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.