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.
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 makes future predictions impossible. Georg argues that software engineering is being commoditized due to the vast amount of training data available (Stack Overflow, GitHub), making AI adept at code generation but raising profound security concerns like prompt injection. Explore: - Why Georg believes blindly adopting AI early is a 'terrible mistake' for most companies. - The fundamental security flaws in LLMs (prompt injection) and why they're currently unsolvable for open input spaces. - The questionable economics of AI: high costs, self-cannibalizing business models, and the reliance on performative fundraising. - How AI tools impact engineer productivity, shifting the bottleneck to decision-making and validation. - The geopolitical risks and diminishing trust associated with Big Tech's AI dominance. - Actionable advice for CTOs: Invest in understanding, focus on governance beyond the tech team, and consider the strategic value of local/open-source alternatives.
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 builds systems to help households manage solar panels, batteries, EV chargers, and heat pumps as integrated energy solutions. He explains the challenges of coordinating with Germany's fragmented energy grid infrastructure and how Enpal's Virtual Power Plant stabilizes the grid by coordinating household energy consumption in real-time. Discover: - 🧠 How Ivan uses intuition as a leadership tool while managing complex technical organizations - 🌞 The technical challenges of building integrated renewable energy systems for households - ⚡ How Enpal's Virtual Power Plant (VPP) helps stabilize the energy grid through coordinated home energy management - 📱 Ivan's personal productivity system and thought management techniques - 🤖 Insights on AI's impact on engineering productivity and the future of coding - 🚀 Practical tips for managing complexity and making decisions in ambiguous environments
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 deep into how freiheit.com has achieved their "Never Late, Never Failed" mission through disciplined processes, carefully selected talent, and a relentless focus on simplicity. Listen to find out 🎯 Why shipping great software is their mission 🧑💻 How they maintain a high bar in recruiting with "tested in life" candidates 📊 Their approach to engineering career levels and continuous feedback 🏗️ Why they prefer full stack engineers over specialized roles 🧩 How they build complex systems from simple components ⚙️ Their custom-built engineering project management tool 🔄 Their program to continually find and remove friction 📈 How they've delivered every project successfully for 25 years 🔍 Why reducing entropy is critical in large software projects 🌐 Why great software should be simple and maintainable for decades
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 companies make sense of AI without the fluff. Together, they explore the latest AI trends, the reality behind AI agents, and how engineering teams can actually get more done with AI today. 🚀 Dat’s journey in AI and tech leadership – From hacking on machine learning before it was cool to leading AI at Axel Springer and co-founding AI startups 🤖 DeepSeek R1’s impact – Why this new Chinese AI model is shaking up the industry and what makes it different from OpenAI’s GPT and Meta’s Llama 🛠️ AI agents & automation – What’s real and what’s just hype? Where do AI agents actually work in business today? 💻 The evolution of coding assistants – How AI tools like Cursor and GitHub Copilot are redefining what it means to be a full-stack engineer 🌍 The global AI race – Is Europe really falling behind? A look at China’s AI boom, US dominance, and what European AI companies need to do to compete 📈 CTO strategies for AI adoption – How to separate hype from real opportunities and where AI can have the biggest impact in engineering teams today If you’re a CTO, AI enthusiast, or just trying to keep up with the latest AI breakthroughs, this episode is packed with insights you won’t want to miss.
How do you create an effective platform team and optimize DevOps? Tobi interviews Camille Fournier about her career, technical insights, and best practices in platform engineering. Camille shares her journey from building her own computers and installing Linux in high school to becoming Managing Director at JPMorgan Chase and authoring influential books for engineers 📚. 👩💻 Camille's early fascination with computers and engineering, including building her own systems and installing Linux 📚 Authoring 'The Manager's Path' and 'Platform Engineering' 🌐 Understanding platform engineering and its evolution from DevOps 🚀 Challenges and strategies in platform engineering for larger companies 💡 Key advice for CTOs on starting and managing successful platform teams
Ever wondered how regulated companies like stock exchanges handle tech growth? Dennis Winter (CTO @ Börse Stuttgart) shares how to build engineering organizations in regulated environments. With experience from embedded systems to leading tech at SolarisBank and Börse Stuttgart, he dives deep into scaling teams while maintaining security and compliance standards 🏦 🏗️ Early-stage tech decisions and building engineering culture 🔄 Evolving team structures and processes as you scale beyond 50 employees 🔐 Security and compliance in regulated environments 🛠️ Infrastructure automation and the importance of early monitoring 🤝 Building team ownership and accountability in regulated companies ⚡️ Role-based access management and device policies
Get insight into the SDK business (and learn about cross-platform performance and developer marketing) with Dr. Daniel Hauschildt (MD & CPTO at IMG.LY). As a client-side offering (no servers!), IMG.LY needs to take extra steps to ensure reliability on all devices 📱, platforms 💻 and browsers 🌐. From crafting developer-friendly documentation to optimizing performance on every device and platform imaginable, Daniel shares hard-earned insights from the SDK business. 👨💻What makes an SDK truly developer-friendly? 🤔 📜Documentation: The secret sauce of INBOUND developer marketing 🔌 API Design: Beauty of purpose-driven entry points 🧩How they build for the future with modular design 🐙 Cross-platform support: Native vs. cross-platform frameworks (React, Flutter etc.) ⚙️Why they focus on algorithm optimization over compute optimisation Listen here: https://alphalist.com/podcast/114-daniel-hauschildt-cpto-imgly
Plan and PRACTICE for better incident response with insights from Tim Armandpour, CTO of PagerDuty. Learn the secrets to resilience from the team that mitigated the impact of a major outage—handling a 250% traffic surge while delivering on their SLA. Listen to find out: - 🛠️ Why planning AND practice are both critical for incident response. - 🚧 How to practice for incident response (e.g Failure Fridays with Chaos Engineering) - 🧑🤝🧑 Ownership: Why tech AND business teams must join post-mortems. - ☁️ How to mitigate the impact of your cloud provider’s lower SLA. - ⚓ Which architectural patterns are more resilient? - ⚖️ WARNING: “bend” the CAP theorem at your own risk Listen here: https://alphalist.com/podcast/113-tim-armandpour-cto-pagerduty
Find out about cross-functional team members with Daniel Bartholomae, CTO at optilyz (direct mail SaaS). At optilyz, team members wear multiple hats—whatever hats they need to own the product lifecycle. From product management and design to development and customer engagement, this model eliminates silos and drives efficiency. Daniel breaks down how this innovative approach works, the tools and processes that make it possible, and why it’s a perfect fit for small B2B SaaS companies. Listen to find out: 🚀 How ‘no product managers’ = efficient ‘sprints’ 🛠️ Why optilyz opts for Miro and Asana instead of Jira 🧩 How to find and hire the right people for cross-functional roles 📜 Architectural Decision Records (ADRs): How optilyz documents technical decisions Listen here: https://alphalist.com/podcast/112-daniel-bartholomae-cto-optilyz
Naeem Sarfraz
A great show, my favourite so far. Lots of nuggets for eng managers.