alphalist.CTO Podcast - For CTOs and Technical Leaders

#133 - Build the Learning Machine: AI Adoption, Flow Metrics, and the Future of the CTO Role with Eric Bowman

From “dangerously skip permissions” to the Andon cord: voluntary adoption, flow metrics, and how agents change what CTOs optimize for Partner Tradegate Direct: Europe’s most direct online broker – trade for free, efficiently, and directly on the stock exchange. Trade directly here [https://tradegate.direct?utm_source=alphalist&utm_medium=podcast&utm_campaign=rb-kampagne-2025&utm_content=dezember-2025] TOPdesk: Discover the future of internal IT in the DACH region with the "Inside ITSM 2026" report – featuring exclusive data on AI, DEX, and collaboration from 6,000 IT professionals. Download the report here [https://www.topdesk.com/de/e-books/inside-itsm-2026-dach/?utm_medium=paid&utm_source=spotify&utm_content=podcast-alphalistcto&utm_campaign=inside-itsm-trends-2026] In this episode, Eric Bowman (CTO @ King.com) breaks down how AI is changing programming, creativity, and technical leadership. We talk about what “living on the edge” looks like with modern AI tools, why “AI is just technology” is still the right mental model, and how CTOs can build organizations that stay fast, adaptable, and focused on time-to-value. We dive into: * Eric’s journey: TomTom → Zalando → CTO at King.com * What “living on the edge” with AI means in real engineering workflows * The future of programming: what shifts when AI becomes a default collaborator * Why AI creativity is different from human creativity (and why that matters) * What an “ideal” tech organization looks like in an AI-first era * Time-to-value and time-to-learning as the CTO’s north star * The Andon cord concept applied to software delivery * How the CTO role evolves as AI reshapes execution, leverage, and expectations * Motivating engineers to embrace AI without turning it into a mandate * Voluntary adoption as a rollout principle (and where it breaks) * Jevons paradox and why “cheaper” AI can still increase total spend * Practical reflections and advice for tech leaders navigating the shift Chapters: [00:53] Meet Eric Bowman: CTO of King.com [02:24] Eric's Journey in Tech [03:25] Living on the Edge with AI [05:43] The Future of Programming with AI [09:51] Navigating the Complexities of AI [22:03] AI Creativity vs. Human Creativity [28:41] Building the Ideal Tech Organization [29:04] Focusing on the Tech Field [29:21] The Future of SaaS [29:50] AI as Just Technology [33:03] Building a Learning Machine [33:32] The Onan Cord Concept [35:29] Time to Value and Learning [38:23] The Evolving Role of CTOs [41:04] Motivating Engineers to Embrace AI [46:02] Voluntary Adoption of Tools [51:35] Jevons Paradox and AI [53:55] Reflections and Advice [56:12] Conclusion and Farewell

#132 - Clarity Over Tooling: Velocity & Building Teams Without Drama with Loïc Houssier // CTO @ Superhuman Mail

From acquisition carve-outs to 100ms interaction rules: Engineering velocity through team clarity, not tool proliferation Partner TOPdesk: Discover the future of internal IT in the DACH region with the "Inside ITSM 2026" report – featuring exclusive data on AI, DEX, and collaboration from 6,000 IT professionals. Download the report here [https://www.topdesk.com/de/e-books/inside-itsm-2026-dach/?utm_medium=paid&utm_source=spotify&utm_content=podcast-alphalistcto&utm_campaign=inside-itsm-trends-2026] Outline How do you maintain execution velocity while building quality products? Loïc Houssier (CTO of Superhuman Mail, formerly Superhuman) offers a contrarian perspective: the answer isn't better tools or frameworks—it's radical clarity about team missions and strategic alignment. With experience spanning French defense contractors (Orange, Thales), navigating DocuSign's complex French acquisition, and now steering Superhuman through its Grammarly acquisition/rebrand, Loïc brings a unique European-to-SF perspective on technical leadership. Key insights for engineering leaders: Execution & Velocity • PR per engineer per week as the "less bad" metric - track trends, not absolutes across teams • Clarity drives speed: clear team missions eliminate dependency bottlenecks and headquarters approval loops • Most velocity gains come from strategy clarity, not tooling improvements • Vertical team alignment: minimize cross-team dependencies by organizing around experiences (calendar team, compose team) • Focus quarterly: solve one major problem per quarter (velocity this quarter, quality next quarter) Technical Architecture Decisions • Monorepo philosophy: resist microservices until genuine pain necessitates splitting • 100-millisecond interaction rule: every UI interaction must complete under 100ms • Offline-first architecture: sync happens in background, all actions execute locally • Gmail/Outlook API integration over IMAP for modern email clients • Modulith with domain-driven design over distributed microservices Team Organization • Guild structure: formalize existing technical conversations (iOS guild, backend guild, AI guild) • Guild leaders surface quarterly problems and negotiate engineering time with product • Platform team + vertical feature teams = minimal dependencies • Full-stack teams owning specific experiences prevent feature factory mentality • Aligned autonomy: clear objectives, flexible execution methods Framework Skepticism • Spotify model: "mostly marketing" according to actual Spotify engineers • GitLab remote-first: ~70% there, not the paradise portrayed • Context matters more than best practices from big tech • Apply frameworks as inputs, not blueprints - adapt to your specific context • Agile manifesto written by senior architects who knew each other - doesn't translate directly to teams fresh from college Product & Design Philosophy • Laser-focused personas (professionals with heavy email volume) vs. Gmail's everyone approach • Four hours per week user time savings from better email UX • Design-centric like Linear: quality experience for narrow audience beats mediocre experience for everyone • Promotion frameworks should align with product goals: bake quality into career ladders if quality matters Acquisition Integration • DocuSign French carve-out: Ministry of Finance blocked some assets, created split structure • Execution during acquisition demonstrates team value beyond revenue/customers • French labor law calculated as risk, not blocker - opportunity cost of not entering EU market • Smooth landings possible: kept redundant roles due to EU market subtleties Cultural Observations • US mindset: "we might die tomorrow" drives urgency vs. EU "we're already successful" complacency • European social safety nets enable higher risk-taking than perceived - losing your job in France is manageable • US risk-taking constrained by healthcare costs, college tuition, lack of safety net • Europeans are "grumpy" seeing empty glass, Americans see half full with optimism Chapters: [00:51] Superhuman, Grammarly, and the rebrand to Superhuman Mail [01:47] Why Grammarly became Superhuman: AI-native productivity suite vision [06:18] Career journey: Math PhD track to security researcher at Orange and Thales [08:18] Submarines and defense contracts: Building the muscle to learn deep tech fast [09:53] DocuSign's French acquisition: Navigating labor law and Ministry of Finance approvals [12:16] Execution velocity: Getting shit done fast as a competitive advantage [15:43] Personal secret sauce: Learning fast, working with smarter people, execution focus [18:58] PR per engineer per week: The "less bad" velocity metric [22:26] Vertical team alignment and minimizing cross-team dependencies [24:22] Monorepo philosophy: Resist microservices until it's genuinely painful [27:02] Framework skepticism: Why Spotify and GitLab models are "mostly marketing" [30:41] Quarterly focus: Solve one major problem every three months [32:30] Guild structure: Formalizing existing technical conversations [36:14] Platform teams + vertical feature teams = ownership without dependencies [38:31] The Linear of email: Laser-focused personas and design-centric approach [40:25] Four hours per week saved: The value proposition for heavy email users [42:05] 100-millisecond rule: Offline-first architecture for instant interactions [46:16] Google's engineer-driven culture and the Gmail maintenance problem [48:38] Promotion frameworks determine product quality [50:02] Career advice: Take more risk in Europe - safety nets enable experimentation

#131 - AI Product Strategy: When to Build and When to Wait with Matthias Keller // CPO @ Kayak

From Alexa to LLMs: Platform experiments, distribution challenges, and how AI is democratizing feature development in travel tech Tradegate Direct: Europe's most direct online broker – trade for free, efficiently, and directly on the stock exchange. Trade directly here [https://tradegate.direct/?utm_source=alphalist&utm_medium=podcast&utm_campaign=rb-kampagne-2025&utm_content=november-2025] In this episode, Matthias Keller (CPO @ Kayak) shares strategic lessons about making AI product decisions under uncertainty. With 12 years at Kayak and experience spanning multiple AI waves—from Alexa to LLMs—Matthias offers a masterclass in knowing when to invest early and when to wait. We dive into: * Strategic framework for evaluating emerging AI platforms (Alexa, ChatGPT, Vision Pro, Apple Intelligence) * Why Kayak's 2016 Alexa experiments failed and what that taught them about timing * The shift from "will this work?" (voice) to "it should work" (LLMs) and why that matters * Competing with distribution giants: Google Flights has massive advantages, so when do you innovate vs. wait? * Real talk on platform bets: early ChatGPT plugins, evaluating ROI on new platforms * How LLMs democratized AI development—engineers now build AI features without data scientists * User expectation shifts: the "why" questions and what they mean for product strategy * Commercial complexity: airlines control content, credit cards worth more than tickets * The "if you build it they may come, if you don't they won't" mindset for CTOs * Balancing first-mover advantage with execution realities in your org This conversation offers actionable frameworks for product and engineering leaders navigating AI strategy decisions. Chapter 1: From Sensors to Travel Tech (00:00 - 09:00) Matthias shares his unconventional path from measuring train wheel vibrations and wireless sensors on mountains to joining Kayak 12 years ago. He discusses the growing complexity of travel booking as airlines unbundled services, creating 15+ ticket options instead of just economy, business, and first class. Chapter 2: Competitive Landscape & Google Flights (09:00 - 13:00) The challenges of competing in a space where Google Flights has massive distribution advantages. Matthias explains how Kayak maintains its edge through innovation like "hacker fares" (combining one-way tickets from different airlines) and comprehensive comparison across hundreds of partners. Chapter 3: Platform Evolution - From Alexa to LLMs (13:00 - 28:00) A deep dive into Kayak's platform experiments, from 2016's Alexa skills and Facebook Messenger bots to today's AI mode. Matthias reflects on what worked (flight tracking), what didn't (voice checkout), and the key differences that make LLMs more successful than earlier voice assistants. Chapter 4: AI Mode & Conversational Search (28:00 - 41:00) How Kayak integrated LLM-powered search across their products, not just as a separate experience. Matthias discusses engagement patterns, the importance of explaining when AI helps versus traditional search, and fascinating user behaviors like asking "why" they should book specific options. Chapter 5: Distribution in the AI Era (41:00 - 46:00) The "dam breaking" moment when airlines and travel providers might embrace AI platforms for distribution. Discussion of commercial barriers, ecosystem control, and how the industry balance between direct booking and meta-search might shift. Chapter 6: AI Democratizing Development (46:00 - 50:00) Matthias explains how LLMs enable software engineers to build AI features without data scientists, using examples like Kayak's price check feature that uses vision AI to compare flight prices from screenshots.

#130 - From PhD Research to DuckDB: Building the Next Generation of Analytical DBs with Mark Raasveldt // CTO @ DuckDB

How single-node performance and embedded analytics are revolutionizing database architecture for modern applications Tradegate Direct: Europe's most direct online broker – trade for free, efficiently, and directly on the stock exchange. Trade directly here [https://tradegate.direct?utm_source=alphalist&utm_medium=podcast&utm_campaign=rb-kampagne-2025&utm_content=oktober-2025] In this episode, we dive deep into the world of analytical databases with Mark Raasveldt, the co-founder and CTO of DuckDB Labs. Mark takes us through his fascinating journey from academic research to building one of the most talked-about databases in the industry. We explore: * How DuckDB emerged from academic research at CWI Amsterdam * The technical philosophy behind embedded analytical databases * Why single-node performance still matters in the age of distributed systems * The challenges of building a database system from the ground up * Open source business models and the DuckDB Labs approach * The evolution of columnar data formats and Parquet optimization * How DuckDB is making high-performance analytics accessible to all developers * The future of analytical data processing and embedded systems This conversation offers unique insights into database architecture, performance optimization, and the intersection of academic research and commercial success.

#129 - $32B Lessons: Building CTO Teams, Rapid Innovation, and Staying Customer-Connected with Solal Raveh

What Wiz's $32B acquisition teaches about scaling CTO teams, rapid innovation, and customer-centric leadership Tradegate Direct: Europe's most direct online broker – trade for free, efficiently, and directly on the stock exchange. Trade directly here [https://tradegate.direct/?utm_source=alphalist&utm_medium=podcast&utm_campaign=rb-kampagne-2025&utm_content=september-2025] What does it take to build a company worth Google's $32 billion acquisition? Solal shares the hard-won lessons from scaling technical teams during one of the fastest-growing security companies in history. Key leadership insights from the episode: • CTO Office Evolution: How Wiz split technical leadership into 3-4 specialized tracks focused on domain expertise rather than geography • The Geographic Cloning Failure: Why hiring locally for technical roles created dissatisfaction and duplication instead of excellence • Remote Team Success: Building global CTO teams around container security, API infrastructure, and runtime protection expertise • Incubation Philosophy: Moving from building teams to rapid POC development - like their 3-hour response to the Shy Hulud NPM exploit • Customer-Centric Engineering: How every CTO team member stays connected to customer challenges rather than waiting for inbound requests • Innovation Metrics: The challenge of measuring incubation success vs finished features, plus P99 performance tracking for enterprise readiness • People-First Leadership: Why focusing on people and customer problems trumps pure technical automation • Security Industry Insights: Making security "not scary" through gamification and community engagement Technical Context (18% of episode): • Agentless API scanning that maps entire cloud environments in minutes vs weeks • Graph database visualization of attack paths from code credentials to AWS admin access • Risk contextualization: Why a CVSS 9.9 vulnerability on unused images can wait, but the same vulnerability across 10,000 live VMs demands immediate action • AI agent "Mika" that correlates threat intelligence with specific infrastructure data Chapters: 1. [01:49] - What makes Wiz worth $32 billion: People and technology combined 2. [04:08] - Technical architecture: Agentless scanning to graph databases to agent validation 3. [10:56] - Personal journey: From assembly coding to customer-focused engineering 4. [14:18] - CTO office structure: Splitting technical leadership into specialized domains 5. [17:30] - Three-fold CTO mission: Foresight, gray areas, and team incubation 6. [19:35] - Evolution from team building to rapid POC development 7. [23:30] - Security industry paradigm shifts: Vulnerabilities, identities, and AI challenges 8. [25:30] - Log4Shell response: Community support and agentless advantage 9. [34:17] - Major failure: Why geographic CTO team cloning doesn't work 10. [40:09] - CTO metrics challenges: Measuring innovation vs finished features 11. [43:16] - Missing hands-on work: The balance between leadership and building 12. [45:44] - Time travel advice: Focus more on people than automation