alphalist.CTO Podcast - For CTOs and Technical Leaders

Pat Casey was the first person besides founder Fred Luddy to write code at ServiceNow back in 2005, when it was called Glide and lived above a friend's restaurant. Twenty years later, he's CTO of a company where 85% of the Fortune 500 are customers, and until recently ran all of engineering: 10,000 people, 7,000 of them writing code. Almost nobody survives the journey from first engineer to public...

Before he founded Render, Anurag Goel was the fifth engineer at Stripe, where he watched roughly a fifth of the engineering team disappear into managing AWS, writing brittle, repetitive, error-prone infrastructure scripts that had nothing to do with the actual product. That experience became the seed for Render: a platform that automates away the undifferentiated DevOps work and lets application t...

Max Deichmann is the co-founder of Langfuse, the open-source LLM engineering platform that became the observability layer of choice for teams building production AI agents, before being acquired by ClickHouse. He started as a business student who taught himself to code via CS50 on a beach in Singapore, pivoted through Y Combinator, fired his own customers mid-batch, and built Langfuse out of a Sun...

Alex Nahas is 28 years old and has already initiated a W3C web standard. Working as a backend engineer at Amazon, he ran into a problem most enterprises face: MCP requires OAuth, but most enterprise infrastructure runs on SAML. His solution was elegant: run the MCP server in client-side JavaScript, letting AI agents use the browser's existing authentication context rather than rebuilding auth from...

Most people assume the web runs on Google. The reality is more concentrated: only three companies on earth operate truly independent search indices — Google, Bing, and Brave. Jean-Paul Schmetz helped build one of them. In this episode, Jean-Paul traces the arc from writing appointment software in a Belgian Radio Shack in 1981, through founding and selling Clix — a European search engine backed by...

Neal Ford: software architect, author, speaker, and independent consultant (formerly 20+ years at ThoughtWorks), joins Tobias to explore what happens to software architecture when AI agents write the code. We unpack the critical distinction between behavior and capabilities: why everyone focuses on what code does, but too few think about scalability, security, and responsiveness. Neal introduces a...

Lee Zen, CTO of Yahoo, joins Tobias to unpack what it takes to modernize one of the internet’s most iconic consumer portfolios—Mail, Finance, Sports, News, and Search—while operating with real legacy constraints at massive scale. We talk about Yahoo’s evolution from its public days to private equity ownership, how modernization actually happens (cloud, platform bets, experimentation), and why ship...

Greg Foster, Co-founder and CTO of Graphite (recently acquired by Cursor), joins the podcast to discuss the massive shift occurring in software engineering: the move from maximizing "Inner Loop" speed (writing code) to solving "Outer Loop" bottlenecks (reviewing, testing, merging). With AI generating code faster than humans can review it, the traditional Pull Request model is under pressure. Greg...

Eric Bowman (CTO @ King.com, previously CTO at TomTom and VP Engineering at Zalando) returns to the alphalist podcast to unpack what “agentic engineering” really means in practice—and how to introduce it to teams without turning it into a mandate. We talk about the uncomfortable trade-offs behind “YOLO mode” tooling, why adoption should feel voluntary even when you set explicit goals (like “five A...

What drives execution velocity—better tools or better clarity? Loïc Houssier, CTO of Superhuman Mail (post-Grammarly acquisition), argues that most velocity problems stem from unclear team missions, not inadequate tooling. From steering DocuSign's French acquisition through complex carve-out negotiations to building Superhuman's offline-first architecture with a 100-millisecond interaction rule, L...

Matthias Keller, Chief Product Officer at Kayak, shares hard-won lessons about AI product strategy and knowing when to invest in emerging platforms. With a PhD in computer engineering from ETH Zurich and 12 years at Kayak, Matthias has lived through multiple waves of AI hype—from Alexa voice skills in 2016 to today's LLM revolution. He discusses the strategic calculus of early platform bets, the p...

Mark Raasveldt, co-founder and CTO of DuckDB Labs, shares his journey from academic research at CWI Amsterdam to creating one of the most innovative analytical databases of the last decade. Mark discusses the technical challenges of building DuckDB from scratch, the philosophy behind embedded analytical databases, and why single-node performance still matters in our cloud-first world. He provides...

What does it take to build a company worth $32 billion? Solal Raveh, CTO Product Infrastructure at Wiz, shares hard-won lessons from scaling technical teams during one of the fastest-growing security companies in history. Learn how Wiz evolved their CTO office from traditional team building to rapid innovation incubation, why geographic team cloning failed spectacularly, and how staying customer-c...

You know how agile transformations always promise better collaboration but somehow teams end up chasing tickets like a factory assembly line? Klaus Breyer from Edding has some thoughts on why this keeps happening—and what actually works instead. Klaus's path to leading product and technology at Germany's most famous pen company wasn't exactly traditional. Before Edding, he spent years managing 40-...

What happens when a distinguished engineer who shaped the cloud-native landscape decides to retire at 42? Kelsey Hightower, a pivotal figure in the Kubernetes community and former Google engineer, shares brutally honest insights from his 25-year journey. This isn't a conversation about the next hype cycle; it's a masterclass in the timeless principles of infrastructure, maintenance, and technical...

How do you drive meaningful AI transformation across 150 software engineers without mandates or force? Peter Gostev, Head of AI at Moonpig, reveals the technical strategies and organizational approaches behind scaling AI adoption from 130 to 400+ users while navigating the gap between industry hype and implementation reality. From managing complex integration challenges where 80% of AI projects in...

What happens when two experienced CTOs sit down to debunk the latest tech trends? Raz Schweiger-Shuty, CTO at auxmoney, joins Tobi for an unfiltered discussion about the hypes, myths, and wastes of resources that plague modern tech companies. After taking over a 17-year-old fintech platform with no prior CTO, Raz made controversial decisions that flew in the face of conventional wisdom: stopping a...

How do you build a foundation model that can write code at a human level? Eiso Kant (CTO & co-founder, Poolside) reveals the technical architecture, distributed team strategies, and reinforcement learning breakthroughs powering one of Europe’s most ambitious AI startups. Learn how Poolside operates 10,000+ H200s, runs the world’s largest code execution RL environment, and why CTOs must rethink eng...

The physical world is becoming digital—and it requires fundamentally different technical architecture than traditional IT systems. Bernd Groß leads technical leaders through the evolution from enterprise software to industrial IoT, where real-time data from 30,000 wind turbines and millisecond-level decision-making define system requirements. As co-founder and CEO of Cumulocity, Bernd has navigate...

Behind the renewable energy revolution lies complex technical infrastructure that CTOs across industries can learn from. Barbara Wittenberg leads a 250-person tech team at 1KOMMA5° that manages real-time data from 40,000+ connected energy assets while coordinating post-merger integration across 80+ companies in 7 countries. This episode unveils the technical architecture powering virtual power pla...

In this episode, Tobi chats with Adam Schuck, Senior Engineering Director at Canva, a company that has scaled to over 5,000 employees, 2,000+ engineers, and 230 million MAUs while remaining profitable. Adam shares his journey through startups (including acquisitions by Twitter and Canva) and large tech companies like Google, leading to his current role managing 220 engineers at Canva. They dive de...

In this episode, Tobi talks with Georg Zoeller, Co-Founder of the Centre for AI Leadership and mercenaries.ai, about the turbulent landscape of AI. Georg, with his background at Meta and deep expertise in AI strategy, cuts through the hype surrounding AI's capabilities and economic impact. They discuss the 'singularity' we're already in, driven by rapid, open-source AI development, and why this ma...

In this episode, Tobi talks with Ivan Kusalic, CTO of Enpal, who leads a team of 250 engineers at one of Germany's leading solar energy companies. Ivan shares insights from his extensive technical leadership journey and his recent return to coding after seven years due to his excitement about AI. Ivan discusses how he navigates complexity and ambiguity in the renewable energy sector, where Enpal b...

Discover insights into building a high-performance engineering organization with Stefan Richter, founder of freiheit.com technologies. With 25+ years of experience delivering successful software projects for the Who’s Who of European businesses and industries, Stefan shares his philosophy of radical engineering culture and maintaining an exceptionally high bar in recruiting. This episode dives dee...

AI is moving faster than ever, and staying ahead of the curve is a challenge for every tech leader. In this episode, Dat Tran joins Tobi to break down what’s happening in the AI space, from cutting-edge model releases to AI-powered productivity tools and the global race for AI dominance. Dat has spent years leading AI teams at Idealo and Axel Springer, co-founding AI-driven startups, and now helps...