How Many CTOs

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub" compare Anthropic and OpenAI's distinct business strategies. While OpenAI takes a high-risk, expansive approach aiming for rapid growth, Anthropic focuses on a more disciplined, business-centric path, particularly targeting corporate customers and avoiding more expensive AI ventures like image and video generation. The conversation extends to thoughts on major tech players like Meta, Microsoft, and Google's positioning in the AI market. They delve into a variety of related topics including the announcement of Google's Flows, Apple's deal with Google Gemini for Siri, and Elon Grokipedia. They conclude with reflections on market movements, investment considerations, and a dose of nostalgia with a nod to Yahoo Pipes. 00:00 Introduction and Welcome 00:34 AI Business Check-In: Anthropic vs. OpenAI 02:10 Anthropic's Cautious Strategy 03:17 OpenAI's Aggressive Approach 05:29 Cursor's Bold Move 08:02 Startup Discipline and Investment Insights 13:04 Apple and Google's AI Strategies 16:38 Google Flows and AI Innovations 17:45 Elon Musk's Wikipedia and AI News 20:10 Conclusion and Wrap-Up Links WSJ: Why Anthropic is On Track to Beat OpenAI to a Profit: https://www.wsj.com/podcasts/whats-news/why-anthropic-is-on-track-to-beat-openai-to-a-profit/9838a414-9082-4a04-9138-9fb390abea2b Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/  Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #AIBusinessStrategies #Anthropic #OpenAI #AIRevolution #AIInsights #TechNews #AINews #AIUpdates

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub delve into Scott's recent meeting with AWS. They discuss the concept of vendors supporting their clients, weighing potential benefits against risks like vendor lock-in and misaligned solutions. The conversation also touches on Scott's old blog 'The Luddite CTO.' They offer practical advice for engineering leaders on framing needs as problems to leverage vendor support effectively, rather than over-functioning or over-committing resources. 00:00 Introduction and Episode Kickoff 00:45 Introducing the Topic: Vendor Support 02:29 AWS's Customer Success Philosophy 03:28 Meeting Breakdown: Challenges and Discussions 05:54 Concerns and Reflections on Vendor Solutions 16:42 Advice for CTOs: Engaging with Vendors 22:53 The Luddite CTO: A Blast from the Past 24:32 The Risks of Cutting-Edge Technology 28:28 Vendor Lock-In: A Real Concern? 33:05 Navigating Vendor Relationships 40:30 Final Thoughts and Farewells Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/  Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #VendorManagement #VendorPartnership #TechInsights #TechSolutions

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub dive into the pervasive influence of AI, starting with a critical look at Apple's Siri and its struggles to keep up with competitors like ChatGPT. They explore the current state of AI and its varied impacts, from productivity boosts in small resource-strapped organizations to the political and societal implications of AI adoption. The discussion also touches on the potential for AI to do good for the world, highlighted by Scott's viral LinkedIn post seeking practical examples. They wrap up with thoughts on responsible AI use, efficiency versus innovation, and the potential benefits for smaller players in the tech landscape. 00:00 Introduction and Welcome 01:27 Apple Siri's Shortcomings 04:42 Public Perception of AI 07:01 Energy Concerns and Data Centers 14:50 Viral LinkedIn Post On AI Innovations 21:41 AI for Dummies: Simplifying Technology 23:58 AI Hackathon: Fostering Innovation 24:58 The AI Boom and Its Societal Impact 26:40 Productivity Gains: A Double-Edged Sword 32:49 The Need for Experts in the Age of AI 38:50 Final Thoughts and Future Plans Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/  Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #AIUpdate #AIDebate #AIProgramming #Innovation #LinkedIn

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss the critical importance of clear requirements in both hardware and software projects. Using the analogy of a home renovation project, they explore how detailed planning and frequent communication between builders and requesters can prevent costly mistakes and ensure customer satisfaction. They relate this to the software development world, emphasizing the need for ongoing dialogue between product managers and engineers to clarify assumptions and avoid misunderstandings. The hosts debate the pros and cons of Agile versus waterfall methodologies and stress the importance of engaging engineers early in the ideation process to harness their technical insights and achieve more efficient, high-quality outcomes. They conclude with reflections on fostering a collaborative culture that values clear communication and thorough planning. 00:00 Introduction and Welcome 00:55 The Kitchen Renovation Analogy 04:59 Drawing Parallels to Software Development 06:21 The Importance of Clear Requirements 19:04 Cultural Challenges in Engineering 31:05 Conclusion and Call to Action Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/  Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #ProductManagement #Agile #ProductRequirements #ProjectRequirements  

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub dive into the 2025 DORA Metrics Report on the state of AI-assisted software development. They discuss key findings such as the near-universal adoption of AI, its impact on productivity, and its role in software delivery instability. Brad and Scott also explore the attributes of high-performance teams and the importance of organizational maturity in leveraging AI effectively. They conclude with reflections on AI's probabilistic nature and its implications for real-world applications. 00:00 Introduction and Welcome 01:08 Dora Metrics and AI: An Overview 03:28 Key Findings from the Dora Report 05:24 AI's Impact on Software Delivery 07:08 Organizational Clusters and Performance 11:00 Foundational Practices for AI Success 13:50 Challenges and Anecdotes 19:32 Challenges in Version Control for Machine Learning Models 23:15 The Importance of Small Batches in Development 25:01 User-Centric Focus in AI Adoption 26:36 Organizational Maturity and AI Success 31:15 AI Usage Statistics and Insights 35:30 Cautionary AI Tales and Lessons 37:22 Conclusion and Podcast Wrap-Up   Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/  Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #AIFuture #DORAMetrics #DORAStateofAIAssistedSoftwareDevelopment #AIAssistance #AISoftwareDevelopment #AISuccess #HowManyCTOsDoesItTake

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub reflect on the recent shifts in Big Tech's approach to AI, discussing the changing perceptions and economic impacts of the technology. They provide insights into the AI hype cycle, comparing it to the dot-com bubble, and ponder whether an AI bust is imminent. They also highlight innovative uses of AI by their colleagues and share interesting articles from Hacker News.    00:00 Introduction and Host Welcome 00:35 AI Roundup: Changing Vibes and Industry Sentiments 02:19 The Hype Cycle of AI 03:32 AI's Long-Term Impact and Comparisons to the Internet 06:15 Economic Implications of AI 10:44 Radiology and AI: Real-World Applications 13:04 Investment and Market Dynamics in AI 14:34 Exploring AI Trends on Hacker News 15:38 Exploring the Cat Cam Phenomenon 17:12 AI Innovations at TaskRabbit 19:18 AI's Impact on Code Quality 22:27 Dealing with AI Naysayers 27:24 50 Cent Adjusted for Inflation 29:15 Podcast Wrap-Up   Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/  Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #AIDebates #AIRoundup #AIHypeCycle #AIInnovations #AIImpact

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub dive deep into the concept of the 10x engineer—those rare developers who are exponentially more productive than their peers. They discuss attributes such as natural talent versus learned skills, curiosity, the ability to think abstractly, and fluidity between high-level design and low-level coding.  As the conversation unfolds, they discuss how understanding the full scope of a system, fostering collaboration, and leveraging the right tools (like debuggers) can elevate an engineer's impact. The conversation turns towards practical advice for identifying and nurturing 10x talent, making it a must-listen for anyone involved in engineering leadership. 00:00 Introduction and Podcast Setup 00:57 Defining the 10X Engineer 01:53 Nature vs. Nurture Debate 02:40 Attributes of a 10X Engineer 19:28 Challenges in Identifying 10X Engineers 23:20 Understanding the Importance of Language in Computer Science 24:16 Identifying Beliefs in Engineering Practices 24:52 The Tabs vs. Spaces Debate 27:07 Continuing Discussion on Attributes of a 10x Engineer 36:26 The Role of Debuggers in Engineering 39:53 Becoming a 10x Engineer 40:30 The Importance of Tools and Pair Programming 43:52 Final Thoughts on 10x Engineers Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/  Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #10xEngineer #TechTalent #NatureVsNurture #Debugging #PairProgramming #SoftwareTools #EngineeringGrowth #InnovationInEngineering  

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub start with a quick retrospective, or is it an encore, of recent rock concerts before stage-diving into a lively discussion about the Software Development Life Cycle (SDLC): what it is, when it matters, and how teams can keep it useful instead of bureaucratic. They explore how the SDLC functions as the connective tissue between engineering, product, and leadership, ensuring teams stay aligned as they grow. Drawing from experiences across startups and mature organizations, Brad and Scott discuss: When and why a documented SDLC becomes necessary How process can scale collaboration without killing creativity The SDLC as a living agreement, shaped by retrospectives and real-world feedback The intersection of feature briefs, technical design docs, and version control Why AI coding agents still need human-governed structure How over-rigid process can backfire — and how to keep the human element front and center They close with reflections on teamwork, accountability, and the shared satisfaction of building something great together. Whether you're defining your first deployment script or revising a 50-page SDLC document, this episode offers practical insight into keeping your software process both disciplined and alive. 00:00 Introduction and Hosts 00:48 Music Talk: Concerts and Bands 05:26 Taylor Swift and Music Industry Insights 08:13 Transition to Software Development 08:32 Understanding the SDLC 10:41 Documenting the SDLC 16:15 Compliance and Security in SDLC 21:02 Product Management and SDLC 28:31 Version Control Chaos 29:26 Deployment Strategies 29:48 The Build Process 30:20 Managing Code Changes 33:36 Commit Messages and Versioning 41:13 The Importance of Requirements 50:50 Challenges in Software Development 55:56 The Team Aspect of Software Development 56:52 Conclusion and Outro Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/ Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #TechLeadership #EngineeringLeadership #SDLC #SoftwareDevelopmentLifeCycle #Compliance #Teamwork #DevProcess #CICD

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub dive deep into the engineering crossroads between Better Architecture Driven Development (BADD) and Feature Driven Development (FaDD). They unpack the eternal question faced by every CTO and engineering leader: Should we refactor now for a better tomorrow, or build features today and clean up as we go? Drawing from decades of leadership experience, Scott and Brad share stories of modernization projects that went right—and wrong. They explore how teams can avoid "second system syndrome," how to build alignment around what better architecture actually means, and why cultural discipline matters more than technical purity. Along the way, they reveal: Why "refactor everything first" often fails—and how to prevent half-finished modernizations. The "While You're At It" risk: scope creep disguised as progress. How executive challenges can sharpen, not derail, technical strategy. The hybrid middle ground—"Bad with Fad"—that blends architectural improvement with feature momentum. Why the fastest way out of a technical hole is to stop digging deeper. Listen in for a thoughtful, funny, and practical debate on what it really takes to evolve complex systems—without breaking the business. 00:00 Introduction and Podcast Setup 00:44 Introducing the Topic: Bad vs. Fad Strategy 01:10 Exploring the Bad Strategy 02:31 Defining Bad and Fad Strategies 03:46 Debating the Pros and Cons 06:15 Personal Experiences with Strategies 08:09 Implementing Better Architecture 16:01 Team Agreements and Practices 18:44 Principles of Software Engineering 19:01 Aligning on Better Architecture 19:37 Challenges in Modernization 22:12 Risks of Bad and Fad 27:31 Hybrid Approach: Bad with Fad 33:29 Cultural Shift for Continuous Improvement 34:53 Conclusion and Reflections Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/ Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #TechLeadership #EngineeringLeadership #SoftwareArchitecture #Refactoring #TechnicalDebt #LegacyModernization #AgileDevelopment #FeatureDrivenDevelopment #BetterArchitectureDrivenDevelopment

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub tackle the evolving landscape of quality assurance in web apps. They challenge the notion of QA as just "manual testers at the end," instead framing quality as a chain of practices across the entire SDLC: requirements, technical design, code reviews, unit tests, automation, monitoring, and stakeholder demos. Topics include: Why QA begins upstream with clear requirements and design, not just testing at the end The role of test automation and real user monitoring (RUM) in catching defects before users do Code review culture as a cornerstone of quality (and why reviewers should run the code) Balancing QA investment for startups vs. enterprise-grade systems A proposed ROI heuristic for test automation (risk, cost of failure, complexity, churn, compliance) The role of AI in QA: pair code reviews, vibe coding risks, and the future of end-to-end automation How context-rich prompts (and even teaching AI like you'd teach a junior dev) improve code quality Why quality assurance is ultimately a cultural mindset, not just a checklist The episode closes with an anecdote on peanut butter & jelly sandwiches, illustrating how precise instructions (and context) are at the heart of both QA and AI development. 00:00 Introduction to User Interaction Testing in AI 00:29 Welcome to the Podcast 00:42 Discussing QA Standards in Web Apps 01:22 Philosophical Approach to Quality Assurance 03:19 Importance of Test Automation and Monitoring 06:15 Real User Monitoring and Production Safety Nets 08:32 Challenges with Requirements and Product Debt 10:10 Sprint Demos and Stakeholder Reviews 15:33 Code Reviews and Implementation Plans 16:59 AI in Code Reviews and Pair Programming 18:39 Balancing Investment in QA for Startups 20:56 Evaluating Risk and Investment in Test Automation 22:47 The Importance of Code Reviews and Unit Tests 26:23 Challenges and Strategies in AI-Driven Development 32:48 The Role of Context in AI and QA 36:20 Concluding Thoughts and Anecdotes Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/ Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #TechLeadership #EngineeringLeadership #SoftwareQuality #QA #QualityAssurance #TestAutomation #CodeReviews #EngineeringCulture #AIinTesting

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub wrestle with one of the industry's toughest questions: How do you measure engineering productivity? The conversation explores the hypothesis that deploy frequency per person can serve as a practical proxy for velocity, and the cultural tradeoffs this metric may introduce. Scott and Brad dig into why smaller, more frequent deploys can drive quality, momentum, and stakeholder confidence, while also acknowledging the risks of discouraging big, bold initiatives. Other highlights include: A step-by-step playbook for turning around engineering teams The dangers of vanity metrics (like lines of code) Why demos beat burn-down charts every time for stakeholder trust The reality (and rarity) of the 10x engineer Balancing incremental progress with audacious projects Selling productivity metrics to non-technical stakeholders Along the way, Scott shares his favorite demo stories (including an on-demand dog-walking product launch at Rover), while Brad offers candid reflections on how teams can avoid paralysis when faced with large projects. If you've ever struggled to explain "velocity" to your CEO or wondered whether deploy counts can really measure productivity, this is the episode for you. 00:00 Introduction: Measuring Productivity in the Industry 00:40 Welcome to the Episode: Light Bulb Jokes and Introductions 01:07 Defining the Problem: Engineering Productivity 03:46 Steps to Turn Around an Engineering Team 04:42 Metrics for Stability and Accuracy 06:34 Hypothesis: Measuring Deploys for Productivity 12:32 Potential Pitfalls and Cultural Impacts 14:33 Balancing Small Deploys with Big Ideas 23:20 Stakeholder Communication and Demos 26:21 Building Inside Out vs. Outside In 27:01 Coolest Demo Experience 28:12 Innovative Home Building Techniques 30:30 Measuring Engineering Productivity 33:42 The Reality of 10x Engineers 40:30 Challenges of Small Deploys 43:46 Selling Productivity Metrics to Non-Tech Stakeholders 47:24 Effective Demo Practices 50:53 Conclusion and Final Thoughts Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/ Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #TechLeadership #EngineeringLeadership #DevOps #Velocity #10xEngineer #EngineeringProductivity #DeployFrequency #CTOlife #DevCulture #AgileLeadership #ProductivityMetrics #TeamVelocity

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub dive into the concept of product debt: what it is, how it differs from technical debt, and why it matters. They unpack how hidden or forgotten product features can quietly slow down innovation, complicate modernization efforts, and create pitfalls when deciding whether to refactor or rewrite. With real-world stories, from duplicate onboarding flows to forgotten VIP requirements, they illustrate how product debt can entangle engineering teams and impact business decisions. Along the way, Scott and Brad explore: The fine line between product debt and technical debt Why modernization efforts often uncover forgotten landmines The risks of rewriting from scratch versus stepwise refactoring How product and engineering leaders can spot and address product debt Why acknowledging product requirements (even undocumented ones) is essential Whether you're a CTO, product leader, or engineer, this conversation offers practical insights into managing complexity, making smarter trade-offs, and leading modernization initiatives with eyes wide open. 00:00 Introduction and Host Welcome 01:18 Defining Product Debt 04:25 Examples of Product Debt 05:51 Technical Debt vs. Product Debt 10:20 Challenges in Modernization 18:07 Avoiding Future Issues 18:34 Challenges of Stepwise Refactoring 19:02 The Hubris of Rewriting 20:24 Undocumented Requirements 21:42 Real-World Examples of Refactoring 24:16 The Complexity of Tech Debt 26:17 Rewriting vs. Refactoring Debate 32:39 Empowering Conversations with Product Debt 33:28 Closing Remarks and Call to Action Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/ Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #TechLeadership #EngineeringLeadership #ProductDebt #TechnicalDebt #InnovationChallenges #RefactorOrRewrite #ProductManagement

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub break down the quirky and serious sides of today's AI. They cover vibe coding, smart glasses, debugging with ChatGPT, and the big question of whether AI gets weaker without human content, offering practical takeaways for CTOs. They tackle topics like: Vibe coding during a meeting: Scott builds a full React Native "streaker" app using Augment Code and Gemini — without touching a line of code. Smart glasses and privacy: What happens when you realize your acquaintance might be recording you in a casual setting? AI safety filters: How clever prompting can slip past restrictions, raising tough questions about the limits of AI guardrails. JSON prompting experiments: Could structured prompts outperform natural language instructions? Debugging with AI: Brad drops raw errors straight into ChatGPT and gets back surprisingly accurate, context-aware fixes. The ouroboros problem: If AI increasingly trains on AI-generated text instead of human-created content, will models eventually get dumber? From practical dev hacks to big-picture concerns, this episode shines a light on the curious intersection of AI technology and human behavior. 00:00 Introduction: A Fun AI Chat Experiment 00:29 Podcast Opening and AI Update 01:15 Hacker News Game: Counting AI Articles 02:52 Smart Glasses and Privacy Concerns 06:06 Vibe Coding: Creating an App During a Meeting 11:12 AI Image Generation: Navigating Content Restrictions 13:43 AI Safety Challenges and JSON Prompting 17:54 Introduction to JSON Prompting 18:03 Examples of Structured Prompts 19:28 Real-World Application of AI Prompts 21:15 Understanding AI's Context Awareness 21:38 Exploring AI's Knowledge Sources 25:17 Personal Experiences with AI 32:55 The Future of AI-Generated Content 39:06 Concluding Thoughts and Reflections Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/ Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #TechLeadership #EngineeringLeadership #AIUpdate #AIDevelopment #AIsafety #JSONprompting #SmartGlasses #GenerativeAI #DebuggingWithAI #VibeCoding

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub delve into the art and science of engineering leveling frameworks. From performance reviews to competency guides, they explore how organizations can fairly evaluate engineers while balancing technical expertise, communication, ownership, and professional judgment. They tackle tough questions like: Should engineering competencies be weighted differently by role or seniority? How do you calibrate across managers to reduce subjectivity? Should engineering managers still code — and if so, when does it help vs. hurt? How do you measure "soft" skills like business acumen or professional judgment alongside technical skills? The conversation also touches on tech debt, culture-building, and frameworks like Dropbox's open-source engineering career ladder. If you're building or refining your engineering leveling guidelines, this episode is packed with practical insights and nuanced perspectives 00:00 Introduction and Employee Growth 00:40 Podcast Kickoff and Banter 01:18 Performance Reviews and Calibration 01:48 Defining Competencies and Calibration Process 06:35 Debate on Weighting Competencies 14:56 Subjectivity in Reviews and Tech Debt Discussion 18:24 Balancing Tech Debt and Business Value 20:23 Prioritization and Professional Judgment 22:05 The Role of Business Acumen in Engineering 24:42 The Importance of Technical and Communication Skills 29:38 Should Engineering Managers Code? 34:36 The Debate on Code Reviews and AI 37:04 Concluding Thoughts and Podcast Wrap-Up Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/ Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #TechLeadership #EngineeringLeadership #CareerFrameworks #TechManagement #EngineeringCulture #LevelingGuidelines #EngineeringGrowth #TechCareers #EngineeringExcellence

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub explore the evolving reality of AI productivity, and what it means for software engineering, product management, and the future of work. They kick things off with a look at recent data showing how the complexity of tasks AI can handle is rapidly increasing—measured by the length of human-equivalent work AI can now complete. This sparks a lively discussion about breaking down work for AI agents, the art of writing effective prompts, and the surprising thoroughness of AI-generated specifications. From there, Brad and Scott share hands-on stories from their own podcast website, revealing how AI coding assistants like Codex and Claude are transforming everything from feature development to bug fixing. The conversation expands into the challenges and opportunities of integrating AI into real-world workflows, the role of design systems, and the shifting responsibilities of engineers in an AI-powered world. Along the way, Scott and Brad wrestle with big questions: How do you break down complex projects so AI agents can succeed? What makes a prompt or ticket "AI-friendly"? Will AI coding agents drive more standardization in software development? How does the engineer's role change when AI handles the heavy lifting? Can AI bring back the joy and creativity that first drew us to technology? Whether you're a CTO, engineer, or product leader, this episode offers a candid look at the practical realities of working with AI, the new skills required, and why embracing these tools might just make your job more fun. 00:00 Introduction and Welcome 00:42 The AI Task Complexity Curve 03:27 Breaking Down Work for AI Agents 08:00 WayMo Traffic Jams 09:05 Real-World AI Coding Stories (Podcast Website Features) 18:04 Standardization, Design Systems, and AI 22:30 A More Complex Example: Episode Transcripts 25:00 AI Agent as Product Manager for AI Coding Agent 28:12 AI Coding Fail, Time for AI Debugging 31:25 Finding Joy in AI-Driven Work 34:50 Outro and Credits Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/ Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #TechLeadership #AIProductivity #AIAgents #PromptEngineering #ProductManagement #Standardization #Coding #AI

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub dig into the messy reality of product management effectiveness, and what happens when bugs reveal deeper product debt. They kick things off with a retrospective on a critical login bug that exposed lingering legacy code, sparking a conversation about how product decisions and technical debt intertwine. From there, the discussion expands into the challenges of measuring product management impact, balancing ROI vs. customer friction, and the growing need for KPIs that capture both engineering and product effectiveness. Along the way, Scott and Brad wrestle with big questions: How do you know if product management is "working"? What KPIs actually measure value delivered versus features shipped? Why do teams struggle to prune software bloat, and what does it really cost? Where should the line be drawn between engineering metrics and product owner accountability? Whether you're a CTO, product leader, or engineer, this episode shines a light on the cost of keeping old features alive, the hidden tradeoffs behind bug triage, and how better metrics can drive smarter product choices. 00:00 Introduction and Welcome 01:09 Incident Retrospective Discussion 05:26 Challenges in Product Management 16:40 Engineering KPIs and Performance Metrics 18:45 Evaluating Product Management Effectiveness 27:28 Closing Remarks and Outro Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/ Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #TechLeadership #ProductManagement #ProductKPIs #EngineeringMetrics #ProductDebt #SoftwareBloat #ROI

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub delve into the critical issue of building a sense of urgency and trust within engineering teams. They discuss the importance of schedule accuracy, delivering on time, and establishing dependable processes. The conversation highlights the essential role of transparency in planning and breaking down large projects into manageable tasks. They explore the impact of culture, environment, and effective communication in fostering a trustworthy and efficient engineering organization. The episode offers insights into overcoming common challenges and bridging the gap between technical and non-technical stakeholders to ensure aligned priorities and timely delivery. 00:00 Introduction and Episode Kickoff 00:56 Discussing Engineering Team Prioritization 01:37 Importance of Schedule Accuracy 03:42 Building Trust with Stakeholders 05:40 Balancing Speed and Reliability 10:19 Collaborative Prioritization with Stakeholders 18:02 Understanding Urgency and Importance 28:09 Vendor Time Estimates and Trust Building 28:53 Evaluating Engineering Team Performance 29:42 People, Process, and Technology Framework 30:52 Team and Environment Alignment 31:52 Impact of Business Environment on Performance 33:40 Urgency and Perception in Engineering 36:24 Breaking Down Tasks for Better Visibility 40:45 Effective Communication with Stakeholders 46:35 Scrum and Agile Practices for Urgency 53:41 Reframing Project Risk and Progress 55:34 Conclusion and Podcast Wrap-Up Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/ Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #SoftwareDelivery #TrustAndTech #UrgencyVsImportance #TechLeadership #AgileDevelopment #ScheduleAccuracy #CTOTherapy

In this "Summer Catch-Up" episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub swap stories from the field, covering everything from data pipeline migrations to the ongoing debate over centralized versus distributed data teams. They explore the critical importance of clear data definitions, the promise (and pitfalls) of data lakes, and how organizational structure impacts collaboration. The conversation shifts into the fast-evolving world of AI in software engineering, with real-world examples of how AI tools are accelerating problem-solving, uncovering hidden performance issues, and boosting productivity across teams. Scott and Brad also reflect on the role of engineering leaders in helping their teams adapt to these tools, not just to deliver value faster, but to future-proof their careers in a rapidly changing tech landscape. 00:00 Introduction and Welcome 00:47 Company Updates and Data Pipeline Migration 01:12 Coldplay CEO Controversy 03:30 Debate: Distributed vs Centralized Data Teams 06:58 Data Definitions and Trust Issues 19:09 AI in Engineering and Toolset Discussion 25:38 Exploring AI in Collaborative Debugging 25:59 Defining Rubber Ducking and Whiteboarding 27:37 AI's Role in Codebase Analysis 29:58 AI Tools and Their Impact on Productivity 37:01 Security Concerns and Tool Selection 41:31 Encouraging AI Adoption in Teams 50:04 The Future of Software Engineering with AI 52:10 Conclusion and Final Thoughts Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/ Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #DataEngineering #DataLakes #AIProductivity #EngineeringLeadership #AIInTech #CentralizedVsDistributed #FutureOfEngineering #TechLeadership #SoftwareEngineering #MachineLearning #DataScience #AIWins

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub welcome design veteran Vince Dean for a deep dive into the shifting world of product design in the AI era. With over two decades of experience across corporate and freelance roles, Vince unpacks how design tools, workflows, and creative expectations have evolved—from Photoshop to Figma, from static mocks to design systems. They explore the unique challenges of designing for connected TV platforms, the rise (and friction) of standardization in design systems, and how AI is both a productivity multiplier and a creative constraint. Vince brings a designer's perspective to questions many engineering leaders are now asking: How much of design can AI automate? Where does human craft still shine? And what does all this mean for the next generation of junior designers? This episode is a must-listen for CTOs, product leaders, and anyone navigating the intersection of design, technology, and artificial intelligence. 00:00 Introduction and Welcome 01:00 Guest Introduction: Vince's Journey in Design 02:33 The Evolution of Connected TV 05:15 Challenges in Design Standardization 10:07 The Role of AI in Design 20:29 Exploring Figma and Design Tools 28:17 Retrofitting Design Systems 28:55 Open Source Design Systems 30:12 AI and Design Systems 31:42 The Role of AI in Prototyping 36:16 AI's Creative Limitations 39:24 Ethical Implications of AI in Design 43:54 Challenges with AI in Visual Design 53:08 Future of AI in Design 54:15 Conclusion and Podcast Outro Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/ Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/ Vince Dean: https://www.linkedin.com/in/vdean/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #DesignPodcast #ProductDesign #DesignLeadership #AIinDesign #DesignSystems #Figma #ConnectedTVDesign #UXDesign #UIDesign #EngineeringPodcast #HumanCenteredDesign #GenerativeAI #DesignCraft #DesignEthics #VisualDesign #DesignTools #CreativeTech #PromptCrafting #FutureOfDesign #AIProductivity #DesignOps #DesignThinking #AIvsHumanCreativity #DesignStrategy #ProductDevelopment

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub are joined by Dan Woods, an expert in founder-led marketing. Dan shares his extensive experience in helping software engineers and product management professionals tell their stories better. The discussion spans Dan's career journey from working on early internet projects like Starwave and thestreet.com, to founding Evolved Media. Dan emphasizes the importance of authentic, founder-driven communication in building an audience and discusses the nuances of applying founder-led marketing in tech companies. The episode also covers the risks and adjustments needed in the traditional playbook for effective founder-led marketing. 00:00 Introduction and Welcome 00:37 Guest Introduction: Dan Woods 00:54 Dan's Early Career and Pre-Internet Era 02:27 The Street.com and Early Internet Journalism 08:58 Transition to Evolved Media 09:49 Founder-Led Marketing Explained 12:36 Challenges and Strategies in Founder-Led Marketing 18:10 The Role of Authenticity in Marketing 20:53 Expanding Founder-Led Marketing Beyond LinkedIn 25:48 Leveraging Founder-Led Marketing for Various Business Needs 29:00 Understanding Client Interests and Passions 30:10 Creating Detailed Personas 32:19 Challenges in Founder-Led Marketing 33:05 The Role of AI in Marketing 34:11 The Future of Marketing: Drama and Storytelling 41:09 Risks and Downsides of Founder-Led Marketing 47:10 Getting Started with Founder-Led Marketing 49:37 Conclusion and Final Thoughts Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/ Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/ Dan Woods: https://www.linkedin.com/in/danwoodsearly/ Evolved Media: https://www.evolvedmedia.com/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #StartupMarketing #FounderLedMarketing #StoryDrivenGrowth #AuthenticMarketing #MarketingForEngineers #EngineeringLeadership #ProductLeadership #FounderBrand #EarlyStageStartups #TechStorytelling #LinkedInStrategy #MarketingPlaybook #BuildInPublic #SaaSMarketing #ContentStrategy #StartupGrowth #MarketingWithAI #EvolvedMedia #ThoughtLeadership