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.

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

How do we actually organize people to consistently deliver value and enjoy the process? This, Eric Bowman (CTO @ King) says, is the core challenge facing any CTO. In this thought-provoking episode, Eric shares insights from his remarkable career in gaming (The Sims, King), e-commerce (Zalando), and navigation technology (TomTom), offering a unique perspective on building high-performing teams and effective tech organizations. Listen in to explore: 🔄 Outcome AND Outputs → Impact (ala Kent Beck’s Universal Value Streams) 🤖 Theory of Adjacent Possibility + Why AI isn’t there yet ⚖️ Product + Tech: Single-threaded (Amazon) vs. Dual Role (Marty Cagan or Google) 🎯 Goals: Kanban-Style Stack Ranking that limits Work-in-Progress 📈 ROI of Tech: Does it increase revenue or speed up delivery? 🧘 Discipline = Action & Commitment + is it time to rethink small teams and platform engineering? Have a listen. Eric has such a great combination of great combination of experience 🦾, knowledge 📚 and wisdom 🧠. Listen here: https://alphalist.com/podcast/111-eric-bowman-cto-king

Become a more effective team in this CTO podcast featuring Rebecca Murphey, Field CTO of Swarmia and co-author of Build. From her years of experience working in the developer productivity organizations at Stripe and Indeed and now at Swarmia, Rebecca knows this conversation isn’t just about developer metrics and productivity - it’s about the broader picture 🖼️. How do we align🧭 our engineering work with with business outcomes💸, developer experience 😀AND developer productivity⚡. And just as important, how do we communicate what we’re doing (and not doing) to other stakeholders? Listen to find out: 🔄 Queuing Theory as paradigm for developer workflow evaluation ⏳ How to allocate time for different engineering tasks 👥 Team Metrics vs. 🧑‍💻 Individual Metrics 📊 Metrics: DORA, SPACE, BRAINs, and more ⚖️ The ethical debate on tracking developer metrics 🤔 If you optimize for the quarter, do you de-optimize for the future? Listen here: https://alphalist.com/podcast/110-rebecca-murphey-field-cto-swarmia-and-co-author-of-build

Save Money on Cloud Costs with Claire Fautsch (CTO @ Joblift). Find out how the team at Joblift slashed monthly cloud costs from €100K to €30K without compromising performance. Listen to find out: 📊 How to build dashboards 📈 How to align cloud costs with business KPIs 🤝 How to get the entire team involved in cost optimization (Spoiler Alert: No FinOps team) 🛠 How to optimize resource allocation and avoid over-provisioning ⚙️ Technical tweaks that made an impact: CUDs, Spot instances, SSD usage, network costs Listen here: https://alphalist.com/podcast/109-claire-fautsch-cto-joblift Brought to you by SmartRecruiters -https://link.alphalist.com/smartrecruiters. Get 10% off when mentioning the alphalist CTO podcast

Keep an eye on the latest trends in this CTO podcast episode featuring Hannes Lenke (CEO and Co-founder of Checkly). Hannes shares insights from over a decade of shaping the testing and monitoring landscape. From AI-powered mobile testing to cloud-based browser testing to synthetic monitoring, he has seen it all. Listen to found out: 👀 What is "Monitoring as Code"? How does it differ from traditional observability? 🔄 Has DevOps changed QA forever? Is there still a place for dedicated QA teams in an automated world? 🚀 How did Checkly evolve into a PLG company with a sales team? ⚙️ How do they run customer code at scale across 21 global data centers? Listen here: https://alphalist.com/podcast/108-hannes-lenke-ceo-co-founder-checkly Brought to you by SmartRecruiters -https://link.alphalist.com/smartrecruiters. Get 10% off when mention the alphalist CTO podcast

Grow the business, not the headcount with insights from Tuomas Artman (CTO of Linear). Saying no to hypergrowth helped Linear succeed, but how did they do it? How did they build a high-quality product with a smaller team? Listen to find out: - How to achieve quality products without increasing headcount 🌱 - Avoiding feature bloat: The pitfalls of customer-driven development ⚖️ - Why you should build for longevity, not acquisition: The downsides of selling too early 🏛 - Why they raised funds after initially planning to bootstrap 💰 - Why Full-Stack Engineers are in 👍, and QA Teams are out 👎 - Why Linear avoids automated UI tests 🚦 - How a local-first synchronization engine ensures a smooth UX ⚙️

Discover new ways to do things with Shyam Sankar, CTO of Palantir, who is working to deprecate backend development using their experience with 150 independent dev teams running a collection of 5,000 microservices. Yet this podcast is more than that (although I was blown away by the demo)—expect great nuggets of wisdom on meritocracy, data, and of course, backend. Think of this podcast as a series of back-to-back nuggets of wisdom that not only help you make sense of what you've observed but also open your mind to emerging trends. Listen to find out 👨‍🍳 How French Restaurants Inspired Engineer-led Sales ⚖️ Finding Success in Contradicting Ideas 🧑‍💻 The Two Types of Engineers: Artists 🎨 vs. Hackers 🔧 🏗️ How he is working on deprecating backend development 📊 Why data is only as good as the decisions it guides and actualizes 📚 The Power of Ontologies 🧩 Inductive vs. Deductive Reasoning 🌈 Diversity in meritocracy through acts of rebellion 💥 ℹ️ Why you need to reduce information asymmetry +🤖 Like Analog to Digital: How LLMs will change things

Find out how to build trust and accountability in a fully remote team in this CTO podcast featuring Sabrina Farmer, CTO @ GitLab. You will also hear how Sabrina draws on her experience in AI, DevSecOps, and her 19 years at Google to rethink the developer experience. Listen to find out: - How Gitlab's CEO Challenge encourages developers to innovate and automate away historic challenges (e.g. Log4js) = Why DevOps is just problem-solving 🕵️‍♀️ at all levels of the stack - How to use AI to create teaching moments 💡 in the developer workflow - How GitLab onboards quicker with detailed documentation📝 (no tribal knowledge)

Discover the benefits of end-to-end technical independence with Alexander Matthey, CTO of Adyen. Learn why Adyen cherishes its in-house strategy as Alexander shares how Adyen’s extreme technical independence (no third-party vendors) enables efficiency in everything from libraries to security. Listen to find out: - Security First: How Adyen makes security a priority for everyone. 🔒 - Pick Up the Phone📞: How direct communication makes them more efficient. - How Adyen’s long-term vision drives innovation. 🚀 - How Conway’s Law is applied to their team structure Listen here: https://alphalist.com/podcast/104-alexander-matthey-cto-adyen?utm_source=feed&utm_medium=referral

Explore the evolution of both a product and the role of its co-founder in this CTO podcast featuring David Cramer (co-founder + CPO @ Sentry). You will discover the pros and cons of each stage in Sentry's journey (open source -> bootstrap -> VC) and why David's role evolved (CEO -> CTO -> CPO). Listen to find out 🔄 Why his role has evolved: CEO -> CTO -> CPO 🧑‍💻 DevTool Marketing 101: Inspiration, Attention, and Conversation 💰 How to monetize open source 🎨 How good branding and design can make an "unsexy" product cool 💳 The power of the self-serve model and its impact on sales 👥 Solopreneur vs. small team with friends ⚖️ Does work-life balance exist in tech? Listen here: https://alphalist.com/podcast/103-david-cramer-co-founder-cpo-sentry

Discover how to leverage platform engineering 🏗️ for convenience, standardization, automation, and reduced cloud costs in this CTO podcast featuring Boyan Dimitrov (CTO @ SIXT). SIXT is a leading global mobility provider serving customers in over 100 countries worldwide. With 800 tech employees globally, they have spent the past eight years standardizing and modularizing their tech stack to achieve unparalleled scalability. Listen to find out: - How to apply the 80:20 rule to Platform ⚖️ - How to automate 🔄infrastructure without tickets 🎟️ - How to reduce cloud costs ☁️with Platform Engineering - How to evaluate ⚖️ an IDP - Why they standardize hosting (cloud and database) 🗄️ - Open Souce vs. Proprietary - Build vs. Buy Listen here - https://alphalist.com/podcast/102-boyan-dimitrov-cto-sixt Brought to you by Storyblok (https://link.alphalist.com/storyblok_podcast)

Get ready for the AI industrial revolution 🦸 in this CTO podcast episode featuring a roundtable of AI AllStars! So much is happening in AI, and you want to be part of it - that is why we asked Jonas Andrulis (Founder and CEO of Aleph Alpha), Rasmus Rothe (Co-founder of Merantix and its AI Campus) and Johannes Schaback (CTO of SumUp) to share with us a broad overview of what CTOs need to know about upcoming AI revolution. Turns out, we aren’t waiting for AGI - we are working on Transformative AI which is in reach for us all. Ready to transform lives with AI? Listen to find out: - ~~AGI~~ Transformative AI by 2030 🤖 - Why your AI strategy (USP💎) matters more than model choice - How to balance AI R&D 🎓with Product 💥and Enterprise Sales 💸 - AI Models: Build⚒️/Buy🛒/Pivot 🧭 - What are emerging opportunities in AI? (Spoiler: B2B SaaS especially in manufacturing 🏭) - How to champion AI 🦸 in your company - Loonshots🚀: how to cultivate innovation - + Hack to attract 🧲 AI talent to non-tech hubs Listen here - https://alphalist.com/podcast/101-ai-revolution-roundtable-feat-jonas-andruilis-aleph-alpha-rasmus-rothe-merantix-johannes-schabak-sumup Brought to you by Storyblok (https://link.alphalist.com/storyblok_podcast)

Trust your intuition, you will gain a lot from this CTO podcast featuring Jason Fried, co-founder and CEO of 37signals, a company known for having groundbreaking policies and products (Basecamp, HEY, Once, etc.). He is also a bootstrapping hero and author of multiple books (Getting Real, REWORK, REMOTE, It Doesn’t Have to Be Crazy at Work). Listen to find out: - Intuitive🔮 over ‘data-driven’ 🔢decision making - Hook 🪝 vs Towel Rail 🎏: The Power of Simple, Versatile Products - CEO-CTO Relationship: How to counteract the negativity brought on by the typical push-pull 🕹️ - Why they do Customer interviews post-launch - Take-home assessments at 37Signals: paid and overloaded 🪨 + Bezos’ shares in 37Signals Listen here: https://alphalist.com/podcast/100-jason-fried-co-founder-ceo-37signals

Lead a more humane and effective organisation with inspiration from Matthew Skelton, co-author of Team Topologies. Inspired by system design💠, cybernetics🤖 and neuroscience 🧠, Team Topologies allows CTOs to structure their teams in a more humane way that reduces cognitive load 🤯 while increasing user value 🎯. Listen to find out: - Value Flow💦: What, why and how to find it - Team Topologies🪢: The 3 team types,1 grouping, and 3 interaction modes - Why Continuous Stewardship 🛞 is important in software - Decoupling🧩 in Time: Amazon’s Secret Source +Why Team Topologies is like Pilates 🏋️ for your company goals🦸 Listen here: https://alphalist.com/podcast/99-matthew-skelton-co-author-of-team-topologies

Embrace the Site Reliability Mindset with Alex Ewerlöf, Sr. Staff Engineer @ Volvo Cars 🚗 and SRE thought leader. Understand how the different aspects of site reliability work together 🪢 and when you need a DevOps vs. Platform Team vs. SRE. Find out how to set your own Service Level Indicators (SLI), Service Level Objectives (SLO), and Service Level Agreements (SLA), as laid out by the creator of the Service Level Calculator. Listen to find out: - SRE 👷 vs. DevOps ⚒️ vs. Platform Engineering🏗️ - Service Level 101: How to set SLIs🚦, SLOs 🎯and SLAs 🤝 - Washing Machine 🧺🫧 vs. Laundry Room🫧🏘️: The Challenges of Standardization - OnCall🎧⚠️: Centralised vs. Team-based? + The unique software challenges of the automotive industry. Listen online: https://alphalist.com/podcast/98-alex-ewerlof-sr-staff-engineer-volvo-cars Read Alex's Website: https://alexewerlof.com. 40% off his book with this coupon code: https://blog.alexewerlof.com/alphalist. This episode was sponsored by DoiT.

Let’s become better Multipliers ✖️ in this CTO Podcast featuring Pat Kua, former CTO of N26 who by popular request now helps CTOs Level Up themselves and their teams. As a sought-after expert in helping ICs transition to leadership roles, Pat shares leadership gems with CTOs. Listen to find out: - Why you should fly high 🕊️and dive deep 🤿 - Why even ICs need leadership skills 🧑‍💻 - Maker⚒️ to Multiplier🌬️: What you need to unlearn when you move into management. - How to communicate: CRY Principle, Translate into Foreign Tongue 💬.. And TCP vs UDP Communication + What the long German Hiring Cycles mean for CTOs Listen here: https://alphalist.com/podcast/97-pat-kua-cto-coach-and-founder-of-the-tech-lead-academy

Discover the power of radical transparency🧐 with Charles Gorintin, CTO of Alan (a French InsurTech) and founding force behind Mistral. He may work in a regulated space, but there is nothing typical about Alan’s setup when it comes to internal matters. Public Salary Framework ✅Searchable Board Meetings ✅4 Managers for 90 FTE✅ Listen to find out: - Why the Manager Role is split into Leads🧑‍💻 and Coaches 🪔 - How Transparent Compensation 💸works with public Salary Levels and Performance Reviews - How he hires 🤝: talent density, culture add and more specialized than him - Why he saw the need for Mistral 🇪🇺 - + How they leverage GitHub Discussions for public decision-making, ownership, and Chesterton’s Fence Brought to you by Instaffo and DoiT

Become a better CTO/CPTO with these insights from David Gebhardt, CTO (and former CPTO) of mobile.de (Germany’s largest car vehicle marketplace). Originally the Head of Tech, David evolved into CPTO, eventually leading the 400-strong Product +Tech teams before evolving business needs led him to bring on a CPO and go back to being ‘just’ the CTO (“only” 250 people). He shares why in this great CTO podcast. Listen to find out: - Why he went from CTO to CTPO and back 🤔 - Self-Efficacy as CTO ✅: How to be effective and FEEL effective - Where innovation 💡 comes from (+ mobile.de’s Innovation Days Format) + Why PHP isn’t all that bad Listen here: https://alphalist.com/podcast/95-david-gebhardt-cto-mobilede Brought to you by Instaffo - https://instaffo.com/cto

Let’s hack cybersecurity in 2024 with Melanie Rieback, Co-founder & CEO of Radically Open Security, the world’s first not-for-profit cybersecurity consultancy with a focus on PenTesting🔏. Melanie is on a mission to fix cybersecurity consulting by putting people before profits and empowering internal teams “how to fish” 🎣. Tune in to hear about the current cybersecurity landscape from the person who not only authored a viral RFID paper (“Is Your Cat Infected with a Computer Virus?”), but also PenTested Tor, Homebrew and Greenpeace. Listen to find out: - What is the business model💸 behind Post Growth Entrepreneurship (90% of profits go towards Open Internet Initiatives via NLNet) - What to prioritise 🕵️‍♀️ in realistic internal IT policies (passwords, backups, updates..) - Internal vs. External Security Teams + Why she uses “Forgot My Password” as a “magic link” to access infrequent sites (and doesn’t remember the password on purpose) Listen here: https://alphalist.com/podcast/94-melanie-rieback-co-founder-ceo-at-radically-open-security

Embrace the technical side 🔧 of the CTO role with Allan Leinwand, CTO of Webflow 🖱️ who has combined technical know-how with great products on every layer of the OSI Model: from setting up HP’s first ethernet, CISCO’s early networks, building the world’s first CDN at Digital Island, and continuing up the stack to enterprise cloud ☁️ (ServiceNow), social gaming​​ 🎮 (zynga), communications 💬 (Slack), eCommerce 🛒 (Shopify) and now webdesign 🎨(Webflow). Listen to find out; - Why deep technical knowledge 🧠 allows better products - How a monolith can combine individual code ownership and great deploy times 🤔 - How to attract 🧲 talent with a ‘boring’ stack (+ Innovation Lab 101) - How to embrace the role of a pre-IPO CTO 🧑‍🚀🚀 - How to stay technical as a CTO 🧑‍💻 - Why he ships small fixes from their #UX-Papercut channel Listen here: https://alphalist.com/podcast/93-allan-leinwand-cto-webflow BROUGHT TO YOU BY: WorkGenius (https://link.alphalist.com/work) and codecentric (https://link.alphalist.com/cc)

Want to become a better manager? Then manage yourself better! From managing the time you spend managing, and all the way to managing how you give your team new tasks... Let's get real with Johanna Rothman, whom they don’t call the Pragmatic Manager for nothing. You will love her straight-talking approach to management. After almost 40 years in management, she can boil down things to sharp principles that will make you either hand pump💯, shoot the link to your buddy🤣… or smile sheepishly🫣. Yip, she got you. (Don’t worry, we won’t judge. Patterns exist because everyone does them. Which is why we need people who have been around the block to call us out 📢on them). Listen to find out: - Why you need to manage yourself to better manage others - Micromanagement: A recipe for multitasking chaos🤯 and WIP overload. - Why Gantt Charts are bad👎. Use Flow Metrics and PERT instead. - Who actually needs to be in the C-Suite (HINT: Not 25 people 🤣) - + how things have changed since the 70s: from the CTO Role to Feedback loops. Listen here: https://alphalist.com/podcast/92-johanna-rothman-the-pragmatic-manager BROUGHT TO YOU BY: WorkGenius (https://link.alphalist.com/work) and codecentric (https://link.alphalist.com/cc)

Empower your team with the right type of autonomy 🚀 as we define the balance in this CTO podcast with Andy Walker, who has years of experience leadings teams at Skyscanner and Google. After 30 years in tech, Andy finally has the time to share what his hard won insights about tech leadership. You will enjoy his nuanced approach to autonomous teams, team size and work-life balance. Listen to find out: Why the more senior you are, the less decisions you should make 🤔 How to give the right amount of autonomy by career stage 🧑‍💻 (and how to have the right conversations about it 💬) How to empower 🚀and support an autonomous team What is the ideal team size?🍕 (What happens beyond Dunbar’s Law?) What motivates your team? 🤗 (SPOILER: Autonomy, Mastery🌟, and Purpose ala Dan Pink) + why Daily Active Users is the Wrong Metric 🫣 Listen here: https://alphalist.com/podcast/91-andy-walker-former-senior-tech-leader-skyscanner-google BROUGHT TO YOU BY: WorkGenius and code-centric

Invest your engineering resources better by truly understanding the core problem your product needs to solve with this CTO podcast featuring Bob Moesta, co-architect of the Jobs to be Done Theory. As an engineer-turned-product-guru, Bob’s explanation of Product Discovery will delight your nerd brain 🧠 (complete with references to set theory, push-pull forces, and the problem space) while being super practical 🔧about the challenges CTOs are dealing with (like scope creep and tradeoffs). Listen to find out: - Why “Build and They Will Come” is a Myth 🫣 - SAM (Serviceable Addressable Market) vs. TAM - Why engineers should be involved in product discovery 🧐 - Customer Interviews: Who to Ask and What to Ask - Why tradeoffs should be influenced by the opinions of those who already bought 🫠 - Hypothesis Building Research vs Hypothesis Proving Research + go inside Tobi’s brain to understand his purchase of his expresso machine. ☕Was it a sudden purchase or were years of ‘forces’ at play? (“The Force(s) made me buy it” 🌬️) Listen here: https://alphalist.com/podcast/90-bob-moesta-co-architect-of-the-jobs-to-be-done-theory

Craft the ideal product strategy in this CTO podcast episode with Melissa Perri, author of “Escaping the Build Trap” and “Product Operations”.Find out how to become truly product-led: from your strategy to your metrics to your tooling. Listen to find out: - How to balance qualitative 😍 and quantitative data 🧪 in product - Were the mass layoffs caused by overhiring? 🫠Is it a natural part of growth or can companies avoid over scaling? - What does the ideal product strategy 🎯look like? - What is ProductOps⚙️ and why you need it - + how to handle your fellow exec’s "greatest idea ever" (AKA Build Trap Alert) 🚧 WARNING: LISTENING TO THIS PODCAST MIGHT CAUSE YOUR PRODUCT STRATEGY TO ACTUALLY BE SUPER FOCUSED AND USED. ONLY LISTEN IF YOU ARE NOT SCARED OF RESULTS. BROUGHT TO YOU BY: [codecentric](https://link.alphalist.com/cc), [Sipgate](https://link.alphalist.com/sipgate) and [WorkGenius](https://link.alphalist.com/work).

Stay on top of your professional development with these learning and productivity tips from Luca Rossi, whose refactoring.club newsletter 🌀 is read by 50k subscribers every week. After scaling Wanderio to 25M users 🚀 as founding CTO, Luca sat down to distill his experiences and in the process created the tech leadership content 📰 he so badly needed. With diagrams. 🖼️ In this alphalist CTO podcast, Luca shares what he has learned about leadership - including the self-leadership needed to structure one's time and effectively harvest the plethora of ideas published online into action. Listen to find out: - What is the flaw in the 'State of Flow"?🌊 - Why CTOs should write more ✍️ - How he structures his day 🌞 - Should CTOs be generalists?🤔 - How he organises his tech leadership 'news clippings' 🗂️ - Tobi getting real 🫣 about recurring 1:1s Listen here: Thank you to our sponsors codecentric, instaffo and WorkGenius