alphalist.CTO Podcast - For CTOs and Technical Leaders

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 shipping velocity becomes the most honest forcing function when you’re rebuilding the engine mid-flight. Finally, we go deep on AI: where it meaningfully improves consumer experiences (mail catch-up, news takeaways, fantasy insights), how teams should avoid “AI labels” without user value, and what it means when AI becomes a tool—and increasingly a coworker.

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 explains how "Stacked PRs" and agentic review workflows are essential for high-performing teams, and why he believes the role of the software engineer is evolving into an "architect of agents." We also cover the strategic rationale behind the Graphite/Cursor merger, the controversial "PRs per engineer" metric, and why he predicts that by 2029, manual code writing will be near zero—but demand for engineers will be higher than ever.

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 AI-assisted commits” as a company-level key result), and why the real opportunity isn’t just faster coding—it’s building a learning system that relentlessly reduces time-to-learning and time-to-value. The conversation spans practical rollout patterns, DORA/value-stream thinking, Toyota’s Andon-cord mindset applied to software, multi-agent decision support with MCP, and why the CTO role may keep converging with product as AI pushes organizations to optimize for iteration speed over output volume.

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, Loïc shares hard-won lessons about engineering metrics that actually matter (PR per engineer per week trends over absolutes), when to resist microservices (until it's genuinely painful), and why promotion frameworks determine product quality. Technical leaders will learn how vertical team alignment eliminates dependencies, why guild structures maintain consistency without blocking speed, and how European safety nets create under-appreciated opportunities for technical risk-taking.

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 painful lessons from experiments that didn't pan out, and how to recognize when technology has truly shifted. The conversation covers navigating distribution challenges when competing with giants like Google and ChatGPT, balancing first-mover advantage with execution realities, and how LLMs are democratizing AI development for engineering teams. Matthias emphasizes the critical framework: "if you build it, they may come—if you don't build it, they won't come."

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 insights into open source business models, the evolution of data formats like Parquet, and how DuckDB is democratizing high-performance analytics for developers everywhere.

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-connected drives product decisions. Discover the three-fold mission of modern CTO roles, the shift from measuring finished features to tracking innovation velocity, and why technical leaders must balance automation expertise with people-first thinking. Technical leaders will gain insights into organizing global remote teams around domain expertise, implementing 3-hour threat response cycles, and building enterprise-ready infrastructure while maintaining startup agility.

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-person World of Warcraft raids (yes, really) and running startups. Now he's applying those lessons to build software teams that actually solve problems instead of just completing tasks. The conversation digs into Shape Up methodology, but more importantly, Klaus explains the mindset changes needed to stop treating software development like an assembly line. His team at Edding has built some pretty cool stuff too—like a B2B driver license verification system using invisible conductive ink that smartphones can read. What you'll learn: • Why "give me a ticket" thinking kills collaboration (even in tiny teams) • How 6-week cycles help teams focus on one problem without distractions • The art of separating problems from solutions before jumping into code • Why late-stage compromises usually mean your team isn't really collaborating • When senior teams can ditch tickets entirely and just... work • Klaus's templates for getting everyone aligned on what problems are worth solving

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 strategy. From the fallacy of technology replacement to the hard business realities that should drive engineering decisions, Kelsey provides a minimalist's guide to navigating complexity. Learn why most companies should embrace managed services, why engineers who can't link commits to revenue are at risk, and what the future of AI really means for the systems we build and maintain. Technical insights for CTOs and engineering leaders: - 🏗️ System Accumulation: Why new technology rarely replaces the old, leading to a complex, multi-generational stack that must be maintained. - ☁️ Managed Services: The economic and expertise-driven argument for outsourcing infrastructure management. - 🔄 Evolutionary Architecture: How to avoid the trap of making permanent technology decisions on day one. - 💰 Business-Driven Engineering: The critical need for engineers to understand revenue, and for CTOs to use business metrics to guide technical priorities. - 🤖 The AI Reality: A grounded take on how AI will impact software, and the fundamental system evolution required for it to reach its true potential."

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 involve traditional software engineering to implementing three-pillar strategies (tool adoption, automation workflows, experimental features), Peter shares hard-earned insights on building AI capabilities through process re-engineering rather than simple automation. Technical insights for CTOs and engineering leaders: • 🏗️ Portfolio approach: balancing quick wins with experimental high-impact projects • ⚡ Prototype-first methodology for validating AI solutions before full development • 🤖 Reality gap between agentic AI hype and production deployment complexity • 👥 Organic adoption strategies that scale without top-down mandates • 🔧 Custom GPT frameworks for non-technical subject matter experts • 📊 Why most AI work is integration, scaffolding, and deployment—not just AI • 🔄 Process re-engineering with AI: changing workflows rather than automating existing inefficiencies

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 microservices migration, questioning Kubernetes adoption, and focusing on measurable business value over engineering trends. His ""dinosaur CTO"" perspective offers a refreshing antidote to tech hype. This conversation cuts through the noise with practical insights on: • 🚫 Why every monolith-to-microservices story ends the same way (spoiler: badly) • 💰 Reducing cloud costs from €120k to €85k through systematic waste elimination • 🔧 When Kubernetes complexity becomes a liability rather than an asset • 📊 Using DORA metrics and cost-per-transaction instead of vanity metrics • 🏗️ Building modular monoliths with domain-driven design principles • 👥 Organizing engineering teams around business value streams, not technology stacks

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 engineering orgs for an agent-driven future.

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 navigated one of tech's most complex domains: connecting industrial hardware through standardized platforms. His journey from Nokia's early cloud computing initiatives to building Germany's leading IoT platform offers unique insights on technical leadership in physical-digital convergence. Technical leaders will gain valuable perspectives on: • 🏗️ Architecting speed-layer systems that handle 50TB monthly data flows while maintaining real-time responsiveness • 🔄 Managing technical debt across hundreds of industrial protocols while modernizing from monoliths to microservices • 🤖 Implementing "AI-IoT" strategies that bridge machine learning models with operational technology deployments • ⚡ Building edge-cloud hybrid architectures for regulated environments and latency-critical applications • 🛠️ Engineering platforms that scale from device management to data operationalization across industrial verticals

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 plants, where millisecond-level responsiveness can prevent grid failures and optimize energy usage. Barbara's journey from electrical engineering to Oracle and Google, then back to energy tech, provides unique insights on combining domain expertise with cutting-edge technology. Technical leaders will appreciate: - 🔄 How to manage distributed systems requiring real-time synchronization across numerous endpoints - 🧩 Strategies for standardizing operations while respecting existing successful processes after acquisitions - 🛠️ Practical applications of AI for automating complex technical explanations to customers - 🌐 Navigating complex regulatory environments that differ by country, region, and technical standards - 🚀 Building technical platforms that unite previously disconnected systems and data flows

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 deep into the challenges and strategies behind Canva's hypergrowth, including: 📈 Scaling engineering teams from 150 to over 2000. 🏗️ Implementing a career framework (Growth & Development Framework) relatively late at 1000+ engineers, moving beyond "minimum viable structure." 🤖 Canva's approach to AI: Viewing it as a tailwind, fostering experimentation ("AI Impact"), providing broad access to tools (Cursor, Copilot, LLMs), and emphasizing human responsibility ("humans as shepherds"). 💻 The core technology decisions enabling Canva's success, particularly the operational transformation logic for real-time concurrent editing and the strategic shift to a unified web-based mobile experience (WebX). ⚙️ Maintaining a startup culture of adaptability despite massive scale. 📅 Adam's personal productivity hacks for leaders, focusing on ruthless calendar management and clear goal setting.