Modern CTO

Albert Strasheim, CTO at Rippling and former leader at Segment and Cloudflare, dives into the pressing cost crisis facing tech leaders today. He reveals how he slashed infrastructure costs by 30% while flawlessly managing a 25% traffic spike. Albert discusses the significance of clear feedback for leadership growth, along with innovative strategies to optimize cloud services and manage AI expenses. He also shares insights on integrating payroll systems, fostering engineering discipline, and the importance of teaching teams about cost impacts.

Brian Elliott, CEO of Blitzy, shares insights on using autonomous software development to dramatically accelerate project timelines. Tom Jackson, CTO at RSM US LLP, discusses the real hurdles of organizational adoption. They highlight how AI agents can compress months of work into mere days and the critical need for effective change management. The conversation dives into strategies for successful pilot teams and the integration of Blitzy’s technology, revealing how they achieved 5x engineering velocity amid real-world challenges.

Rob Duffy, CTO at HealthEdge, is a tech leader specializing in AI and healthcare technology. He discusses why flashy AI demos often fail to produce real ROI and emphasizes treating AI migration with the same carefully structured approach as cloud migration. Duffy advocates for grassroots adoption at HealthEdge through a pilot program and stresses the importance of leaders using AI tools to drive change. He also highlights the need for cultural shifts in engineering roles and the value of quickly experimenting with multiple AI projects to understand effective strategies.

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.

In a unique year-end awards discussion, hosts crown the Modern CTO of 2025. They delve into standout moments from the year, from bold AI strategies to unconventional leadership advice. Insights on ethical implications of grief-AI spark debate, while creative hiring tips and storytelling take center stage. A humorous clip about removing sugar lightens the mood, culminating in the announcement of Rob Duffy as the award winner for his impactful AI adoption. Plans for future content keep the excitement brewing!

In this engaging conversation, Chris Barton, the visionary founder of Shazam, shares the incredible journey of transforming a four-digit phone service into a $400 million app. He reveals the challenges Shazam faced during six years of losses and how the launch of the App Store became a game-changer. Chris also discusses the magic behind the app's name, the innovation of robust audio fingerprinting, and the critical lesson of eliminating user friction for massive adoption. His insights underscore the blend of perseverance and creativity in tech entrepreneurship.

Celebrate the season with a festive greeting from the hosts! They share exciting previews of next week's nostalgia, highlighting Chris Barton's journey in building Shazam, culminating in its impressive $400 million sale to Apple. The hosts also sprinkle in some heartfelt holiday wishes, leaving listeners eager for what's to come.

In this engaging conversation, Micha Kiener, CTO at Flowable, shares his expertise in business process orchestration. He discusses how Flowable transformed customer onboarding from five days to just seven minutes. Micha emphasizes the importance of orchestration over mere automation, explores the concept of agentic AI, and explains how proper context engineering can enhance performance. He also touches on challenges like regulatory fragmentation and the need for enterprise readiness to thrive in the evolving tech landscape.

In this engaging conversation, António Vieira, Director of Global Apps Engineering at Sky, shares insights on scaling the Peacock streaming service to handle millions of users. He discusses the complexities of live streaming compared to video on demand, revealing how they manage 30% of internet traffic during major NFL games. António also dives into AI's role in personalizing viewer experiences, from synthetic voice recaps to innovative real-time features like multi-view highlights. His perspectives on leadership and engineering culture are both inspiring and thought-provoking.

Sam Ransbotham, AI editor at MIT Sloan Management Review and host of the Me, Myself, and AI podcast, delves into the evolving relationship between humans and AI. He highlights that 76% of executives now consider AI as coworkers rather than tools. Sam discusses the challenges of outdated healthcare privacy laws in the age of advanced AI and presents insights on how cheaper coding is predicted to create programming jobs. The conversation also explores the implications of agentic AI adoption and the future of organizational design.