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How Many CTOs

Brad Hefta-Gaub & Scott Porad

Welcome to the "How Many CTOs?" Podcast, hosted by Brad and Scott, where we dive deep into the intricate world of Chief Technology Officers. Each episode features candid conversations with guest CTOs who share their real-world experiences and insights on a wide range of topics. From building and upleveling high-performing engineering teams to managing and communicating the impact of tech debt, we cover it all. Discover strategies for measuring engineering productivity, refining processes, and balancing innovation with structured methodologies. Learn from experts about decomposing monolithic systems and keeping up with the latest technology trends. Whether you're a current or aspiring CTO, our podcast offers practical solutions and valuable advice to navigate the ever-evolving landscape of technology leadership. Tune in and join the discussion on overcoming the common challenges faced by CTOs today. Don't forget to subscribe, rate, and review! #TechLeadership #CTO #techpodcast

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  • 24 episodes
  • weekly
  • Avg 47 min
  • English

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  • S2 · E35
    September 8 · 50 min

    Beyond Cost Reduction: AI in Revenue Generation and Innovation with Andy Boettcher

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub interview Andy Boettcher, Chief Innovator of DoubleTrack, a boutique data and AI consultancy. Andy recounts his 33 years across systems, development, with 13 years in Salesforce, and how his career shifted into data/AI full-time after ChatGPT's 2022 release. The group compares manufacturing's precise cost estimation to software's people-driven unpredictability, then explores moving beyond AI for cost takeout toward top-line revenue lifts. Andy emphasizes mindset—curiosity, open-ended questions, and "always assuming you're wrong"—and argues resistant engineers will be replaced by those using AI. They discuss using AI as a peer, agentic workflows, real-time CX intelligence for renewals/upsell, ethics, and the need for human-in-the-middle quality gates, scoring rubrics, and trustworthy PR artifacts. 00:00 Cold Open 00:18 Meet the Guest Andy 02:15 Micro Estimating Story 04:17 Why Software Estimates Fail 05:55 DoubleTrack and AI Work 08:15 Revenue vs Cost Takeout 10:39 AI as Peer Partner 13:35 Curiosity New Mindset 17:30 Learning to Prompt Better 20:49 Agents and Orchestration 23:05 Managing Teams of Agents 25:09 Real Time CX Signals 27:09 Scraping The Corners 29:07 Ethics Of Live Upsell 30:17 Async Agents In Practice 34:47 Trust And AI Slop 40:29 Agent Driven Code Reviews 44:52 Rubrics And Quality Gates 48:24 Final Advice And 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/ Andy Boettcher: https://www.linkedin.com/in/andyboettcher/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #AIAssistedCoding #AIAssistedProgramming #AIProgramming #AICoding #Innovation #Data #RevenueGeneration #MachineLearning #BusinessStrategy #DataAnalytics #BusinessGrowth

  • S2 · E34
    September 1 · 52 min

    The Hardware/Software Blend: Visionary Innovations in Health Tech with Eyebot's Jack Moldave

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub interview Jack Moldave of Eyebot, a company he co-founded nearly six years ago to make getting glasses as easy as buying shoes by enabling on-demand vision tests and prescriptions in retail settings. Jack explains Eyebot's kiosk experience in Walmart Vision Centers, including intake questions, visual acuity testing, touch-free refraction and glasses scanning, and remote review by licensed optometrists/ophthalmologists with prescriptions returned in under 15 minutes. He discusses navigating FDA regulation as a Class I medical device using risk assessment (FMEA), a quality management system, and traceability, and shares why venture capital helped fund regulated hardware R&D. The conversation also covers Eyebot's doctor portal and network, limits versus comprehensive eye exams, potential future screening as a Class II device, and the challenges and culture required to merge hardware and software development with over-the-air updates and manufacturing partners. 00:00 Podcast Cold Open 00:51 Eyebot Mission 02:04 Founders and Origin 04:43 Access Stories 07:19 FDA Basics 10:30 FMEA Risk Analysis 13:17 Quality Systems 15:43 Funding Realities 16:53 Walmart Kiosk Flow 20:29 Touch Free Design 23:50 Remote Doctor Network 26:57 When to Refer Out 27:48 Minotaur Care Model 28:48 Doctor Shortage Solution 33:38 Hardware Software Moat 35:05 Formlabs Playbook 38:46 Leasing and Upgrades 40:11 First Launch with Walmart 48:35 Suppliers and Scaling 49:52 Culture and Closing 51:53 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/ Jack Moldave: https://www.linkedin.com/in/jackmoldave/ Eyebot: https://www.eyebot.co/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #AIAssistedCoding #AIAssistedProgramming #AIProgramming #AICoding #VisionCare #Innovation #MedicalDevice #Eyebot #EngineeringExcellence #HardwareDevelopment #SoftwareIntegration #DigitalHealth #FutureOfHealth #RegulatoryChallenges #EngineerSpeak #TechSolutions #MedTech #HealthcareInnovation #VisionCareAccess #MedDevice #SoftwareHardwareBlend

  • S2 · E33
    August 25 · 16 min

    Fast, On Time, or Fully Utilized? Choosing What to Optimize in Engineering Delivery

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss a leadership conversation where three senior stakeholders wanted different outcomes from engineering: delivering faster, maximizing utilization, or delivering on time—highlighting unclear norms and expectations in the software delivery system. The hosts argue you can't optimize all three at once, note that maximum utilization is a poor goal (systems perform better below 100% utilization), and debate prioritizing speed versus schedule. Scott favors being on time with about 80% accuracy to avoid sandbagging and support business dependencies like launches, while Brad generally prioritizes going fast, especially in early-stage or learning-focused contexts, with "within reason" expectations. They add an unspoken distinction between innovation organizations and manufacturing organizations, and observe that projects often go off schedule due to unclear requirements, shifting scope, or faulty early assumptions. 00:00 Cold Open 01:04 Velocity Tradeoffs Debate 03:07 On Time 80 Percent Rule 03:56 Innovation Versus Manufacturing 05:03 Why Utilization Misleads 06:43 Stage Dependent Speed 09:32 Quality And Launch Systems 11:56 One Project Always Late 12:51 Why Projects Derail 14:41 Front Load The Hard Parts 15:50 Wrap Up 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 #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #AIAssistedCoding #AIAssistedProgramming #AIProgramming #AICoding #Velocity #Productivity #Utility #ResourceManagement #GoFast #GoFastBreakThings #ProductManagement #SpeedVsAccuracy #InnovationCulture #Innovation #EfficientTeam #Efficiency

  • S2 · E32
    August 18 · 56 min

    The Pace of Innovation: Systems Thinking for Faster Engineering

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub open with travel and sports talk, including World Cup rules, then pivot to Scott's change-management training on systems thinking and unspoken norms. They explore a meta-question: if non-engineering teams couldn't tell engineering to "go faster," what would they change to increase engineering throughput? Using AI as a lens, they argue the bottlenecks become: deciding what to build, keeping a prioritized "shovel-ready" backlog, and handling downstream constraints like training users, releases, and integrations. They emphasize learning feedback loops, including studying what went right, and discuss long-horizon thinking for durable platforms. The conversation touches on Spain's mail-based customer service requirement, balancing innovation vs basic fixes (TaskRabbit categories), intentional tech debt, and ideas from Eric Ries's book "Incorruptible," plus examples of enduring companies like Costco and century-long businesses. 00:00 Cold Open 00:31 Podcast Kickoff Banter 00:44 Mountain Adventure Recap 01:37 Sports Week Highlights 03:53 Change Management Systems 05:10 Elevator Norms and Rules 07:51 Meta Question On Speeding Up Engineering 09:56 Instant Code Bottlenecks 12:03 Shovel Ready Planning 14:29 Downstream Release Constraints 19:35 Build the Right Stuff 24:59 Learning Loops and Postmortems 28:01 Spain Side Quest 30:23 Stop Forcing Revenue Targets 34:01 Mission Metrics And 3M 39:42 Innovation Versus Basics 42:37 AI Changes Tech Debt Math 49:03 Think In Decades 53:38 Costco Mission And Hotdogs 56:00 Subscribe 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 #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #AIAssistedCoding #AIAssistedProgramming #AIProgramming #AICoding #EngineeringInnovation #SystemsThinking #R&D #Innovation #ProductManagement #ResearchandDevelopment #BusinessStrategy

  • S2 · E31
    August 11 · 45 min

    Method to the Madness: A CTO Framework for Systemic AI Adoption

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss how CTOs must frame narratives that help teams organize around ideas, inspired by how Scott explained his company's AI work to a non-technical friend. The hosts outline four intertwined AI workstreams: getting AI to handle increasingly complex engineering (from functions to features to systems), moving toward autonomous "dark factory" software development, scaling AI adoption through standards and systems (shifting from organic experimentation to systemic usage, like AI code review and possible security/architect review agents), and managing token spend, including discussion of token-maxing incentives, looping, and interest in local inference and vendor lock-in mitigations such as AWS Bedrock. The episode also includes numerous anecdotes from the hosts engineering teams and time as parents. 00:00 Cold Open 00:45 Recharge Week Catchup 02:02 Sapiens and Storytelling 03:14 Cognitive Revolution Explained 05:11 AI Elevator Pitch At Baseball Game 06:42 Three AI Workstreams 10:35 Complex Engineering with AI 11:30 Building SaaS with Agents 13:05 Dark Factory Automation 14:30 Scaling Standards and Systems 17:41 Organic to Systemic Adoption 19:41 Scouts and Shared Conventions 20:49 Spec Driven Development Debate 21:33 Middle Ground of Feature Brief 23:31 Security and Architect Agents 25:02 Token Spike Story 28:42 The Innovation of Reuse 29:40 Token Management Debate 33:08 Looping Burns Tokens 35:09 Local Inference and Privacy 38:43 Vendor Lock In and Bedrock 41:58 CTO Narrative and Framework 44:32 Wrap Up 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 #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AIRevolution #Automation #TokenManagement #AIInnovation #ComplexEngineering #AIAdoption #FutureOfAI #TechEnthusiast #VendorLockIn #EngineeringExcellence #SoftwareStrategies #AIInsights #CTOCommunity #AIStandards #TechPodcast #EngineeringLeadership #OrganizationalChange #AI #AIAssistedCoding #AIAssistedProgramming #AIProgramming #AICoding

  • S2 · E30
    August 4 · 1 hr 1 min

    There's A Pattern To Follow: An Interview with Robert "Uncle Bob" Martin

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub are honored to interview Robert "Uncle Bob" Martin, who recounts his 60+ year programming journey from a three-bit binary device and years of assembly to C, C++, and Java, to now using AI agents to code. He explains how the Agile movement emerged from the design patterns community, Extreme Programming, and the 2001 Snowbird meeting that produced the Agile Manifesto. He argues Agile arose as a response to failed upfront analysis/design and emphasizes feedback, small iterations, and early discovery of uncertainty, while noting Agile was later overtaken by project managers and certification-driven Scrum. Martin discusses the ongoing tension between business roadmaps and engineering uncertainty, advising ranges over firm dates, and connects Agile lessons to AI coding: neither big upfront specs nor "vibe coding" works without strong engineering disciplines enforced by deterministic tools (tests, static analysis, CRAP metric), enabling developers to step back from reading syntax while still guiding quality. The episode ends with a discussion on the future of training engineers and the possibility of an apprenticeship model of learning. 00:00 Cold Open 00:20 Meet Uncle Bob 01:24 First Computer Memories 03:19 From Assembly to C 05:04 Coding With AI Agents 07:00 How Agile Was Born 12:04 Why Waterfall Failed 19:01 Agile Gets Hijacked 21:23 Roadmaps vs Reality 26:21 Agile Lessons for AI 30:52 Agent Myopia Risks 31:40 Deterministic Tooling 32:48 CRAP Metric Whip 34:29 I Don't Read Code 38:14 Assembly to C Lessons 41:29 Abstraction History Repeats 43:14 AI Broke The Plateau 48:09 Agents In Practice 52:14 Quality Gates For All 56:03 Training New Engineers 58:26 Apprenticeship Model 01:00:38 Closing 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/ Bob Martin: https://x.com/unclebobmartin Bob's book: Clean Agile: Back to Basics #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #AIAssistedCoding #AIAssistedProgramming #AIProgramming #AICoding #Agile #UncleBob #AgileManifesto #AgileDevelopment #AIRevolution #FutureOfTech

  • S2 · E29
    July 28 · 43 min

    Is Uncle Bob Right? Reading Code vs. Architecting the Future

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss how Robert "Uncle Bob" Martin—author of Clean Code and Agile Manifesto signer—sparked online controversy by saying he no longer reads the source code produced by his programming agents. They unpack his argument that strong "control systems" like automated unit and end-to-end tests, static analysis, and architecture acceptance criteria can replace line-by-line review, shifting human attention to higher-level architecture and justification. The hosts debate the limits of this approach in legacy systems lacking tests, explore how CTOs create quality through hiring and checks-and-balances, and emphasize spot-checking high-risk work such as one-way-door decisions, infrastructure migrations, data model design, and surprising estimates. They also consider building architecture/security agents and why Uncle Bob's opinions carry influence. 00:00 Podcast Kickoff 00:58 Who Is Uncle Bob 03:01 Agentic Coding Controversy 04:18 Quality Controls Over Reading 06:39 Legacy Code Testing Problem 09:49 Belligerents in the Debate 10:47 What Code Reviews Catch 12:31 Agents for Architecture Security 15:35 Multiple Reviewers Probability 17:41 CTO Checks and Balances 18:48 AWS Region Move Rollout Plan 20:27 Data Center War Stories 22:16 Reviews as Conversations 23:15 Beyond Reading Code 24:11 Presenting Upward Forces Clarity 25:44 CTO as Company Voice 27:49 Spot Checks and Breakpoints 29:11 When to Dive In 30:05 Data Intuition Stories 33:08 Debugging Big Estimates 36:08 Uncle Bob Agents 39:39 Why We Care 42:05 Wrap Up 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 #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #AIAssistedCoding #AIAssistedProgramming #AIProgramming #AICoding #UncleBob #Agile #AgileManifesto #CleanCode #AIAgents #CodingRevolution #AIinTech #LegacySystems #QualityControl #AgenticProgramming #EngineeringExcellence #TechDisruption #ProgrammingWisdom #AgilePrinciples #CodingGiants #TechEvolution #ModernEngineering

  • S2 · E28
    July 21 · 1 hr

    Token Maxxing and Local Inference: Navigating the Shift in AI Usage for Developers

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss token spending and the "token maxing" backlash, sparked by a GitHub Copilot budget issue and broader industry moves to optimize tokens. The hosts argues companies should focus on value and learning rather than premature token optimization, while still adding circuit breakers to prevent runaway costs. They explore shifting to local inference and open-weight/open-source models for cost, privacy, and control, citing concerns about vendor policy changes like Fable's retention and classifier behavior. The conversation expands into how AI shifts bottlenecks from coding to product management, experiments pairing product and engineers using SpecKit, and how AI may realize Agile's iterative promise. They close on distribution as a key frontier and the career opportunity of being early in AI, likening it to the early internet era. 00:00 Cold Open 00:27 Podcast Kickoff 00:46 Anniversary Trip in Maui 02:54 Copilot Budget Surprise 05:15 Token Panic Backlash 07:54 Value Over Tokens 13:33 Local Models Rising 15:46 SaaS Apocalypse Talk 17:29 Cycle Time vs Value 20:19 SpecKit Pairing Experiment 22:43 AI Meets Agile Promise 24:50 Spec First Agile Debate 29:40 Builders VS Managers 31:40 Scaffolding Vibe Coders 32:29 Distribution Is Hard 35:51 Snoring App Niche 38:43 Targeted Ads Reality 40:07 Open Source Pushback 42:11 Three Pressures On CTOs 44:56 Privacy And Data Control 53:38 Frontier Models Trust Issues 56:19 Three Truths For Teams 58:09 Early Internet Lessons 59:44 Wrap Up 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 #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #Entrepreneurship #TokenMaxxing #LocalInference #AI #AIProgramming #AIAssistedProgramming Agile #Innovation #OpenSource #Privacy #OpenWeight #AIRevolution #Leadership #Innovation #AgileDevelopment

  • S2 · E27
    July 14 · 56 min

    This Has Always Been A Problem: Slot Machine Devs and Growing Junior Engineers in the Age of AI

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss how managing armies of coding agents can be physically draining, likening it to context switching in flat organizations. Scott references Yuval Harari's "Sapiens," connecting the cognitive and agricultural revolutions to modern pressures. The hosts debate whether AI causes coding skills to atrophy and blocks junior engineers from becoming seniors, framing "pulling the slot machine lever" as shipping code you don't understand. Brad shares a pre-AI story about copying Stack Overflow code for a 3D triangle point test, leading to lessons about ambiguity and understanding. They argue this cargo-cult behavior predates AI, though AI makes laziness easier, while curiousity can accelerate learning. They also discuss "taste" as effective engineering opinions, shifting skills toward interrogating LLMs, and a potential K-shaped industry split between WYSIWYG builders and engineers closer to the metal. 00:00 Cold Open 00:21 New Listener Surprise 01:36 Managing AI Agents Burnout 04:26 Sapiens and Cooperation 07:46 AI Complaints Are Engineering 08:49 Slot Machine Coding Metaphor 09:41 Stack Overflow Triangle Story 15:41 Cargo Culting and CopyPasta 16:30 Juniors to Seniors in AI Era 23:42 Curious vs Lazy AI Use 27:08 Models Improve and Safety 28:39 Engineering Is Shaping 29:58 Junior Vs Senior Judgment 31:03 What Is Taste 34:22 Engineering Job Shifts 37:25 Curiosity Still Wins 39:59 Build Stuff To Grow 44:04 Learning Through Debugging 46:25 Managing LLM Atrophy Risk 49:55 Pair Programming And Market Pressure 53:31 K Shaped Future 55:29 Wrap Up 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 #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #StackOverflow #CargoCulting #JuniorvsSeniorEngineers #JuniorEngineers #SeniorEngineers #AI #AIProgramming #AICoding #AIAssistedCoding #AIAssistedProgramming #SlotMachines #InnovationVsComplacency #ProgrammingLife #CodingChallenges #ArtificialIntelligence #LazyCoding #SoftwareSkills #AIInCoding #EngineeringChallenges #DeveloperJourney #InsideTech

  • S2 · E26
    July 7 · 51 min

    From Chaos to Control: Bringing Specification Driven Design to Vibe Coding with David Bauer

    In this episode of "How Many CTOs Does It Take?" podcast, host Brad Hefta-Gaub is joined by Dr. David Bauer of Axonis AI, who shares how his background in distributed computing, startups, and the U.S. intelligence community led him to Axonis AI's federated data layer used for federated learning, data fusion, semantic ontologies, and decision intelligence. Bauer describes how encouraging engineers to use any LLM tool led to incorrect, unreviewable PRs and broken releases, especially in security-critical areas, as MCP tooling sprawl made tool selection unreliable. Axonis rebuilt its development workflow around specification-driven design with extensive automation, agentic workflows, Git hooks, and spec-centric Agile tracking, shifting engineers from code-centric work to "vibe speccing" and system understanding. They prioritize end-to-end integration tests as the primary quality gate, keep integration test implementations tightly controlled, and automate much of GitLab interaction while using their own compliance/attestation tooling to tie decisions to evidence across the company. Brad and Bauer engage in a healthy debate about the need for unit tests in the age of AI-assisted programming, and they end the episode by discussing how to empower engineers who focus on identifying and solving business needs, rather than the minutia of the actual coding. 00:00 Cold Open 00:27 Meet Dr David Bauer 01:15 Axonis AI Origin Story 02:54 Why Startups Must Use AI 04:42 When Vibe Coding Breaks PRs 07:29 Team Scale And Pain Points 08:29 MCP Tool Sprawl And Gateway 10:21 Specification Driven Design Fix 18:49 Quality Gates And Integration Focus 21:44 Unit Tests Debate Begins 26:22 Robot Test Validation 28:04 Unit vs Integration Tests 29:51 Vibe Speccing Workflow 32:52 Engineers as PMs 34:55 Compliance Tooling Attestations 38:36 Federated Data Evidence 40:17 Advice for Engineering Leaders 43:24 Specs Beyond Engineering 45:56 Making Specs Consumable 49:26 Wrap Up and Credits Resources: How Many CTOs Pod: https://howmanyctospod.com Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/ David Bauer: https://www.linkedin.com/in/dr-bauer/ Axonis AI: https://www.axonis.ai/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #VibeCoding #IntegrationTesting #AI #AIAssistedCoding #AIAssistedProgramming #ProductDevelopment #Agile #SpecificationDrivenDesign #SystemDesign #AIInTech #AgileProcesses #LeadershipDevelopment #ContinuousIntegration

  • S2 · E25
    June 30 · 49 min

    Introducing Skein and Beaker Stack: Using AI Agent Engineers to Ship SaaS Faster

    In this special episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss Brad's experiment proving that AI can dramatically boost output for teams with strong engineering practices. Brad shares an MIT-licensed open-source SaaS template called Beaker Stack, which includes web and mobile scaffolding, CI/CD for preview/staging/production, automated setup, observability, email tooling, and Stripe-based tiered billing with feature gating. He then uses it to build Skein, a cloud-hosted shared "memory backplane" served via an MCP endpoint that lets multiple AI tools and agents read/write memories with strong security controls and auditing. Brad describes hiring four AI agent "engineers" (Diego, Mei, Rahul, Sarah) with persona "soul files," running them in Nanocloud/Nanoclaw containers for security, coordinating work via Telegram and GitHub, and applying spec-driven, test-heavy guardrails to ship Skein in about 10 days of part-time work. Scott asks questions about Brad's process, and the two hosts debate how different perspectives effect an engineer's process, be they AI agent or human coworker. A video version of this episode can be found on the How Many CTOs YouTube channel! 00:00 Cold Open 01:05 AI Velocity Thesis 02:16 Shipping SaaS Every Six Weeks 04:37 Beaker Stack Tour 08:11 Meet The AI Engineers 09:52 Agent Workflow And Reviews 12:11 Building Skein Shared Memory 14:45 10 Day Build And Metrics 18:51 How Skein Uses Beaker Stack 24:20 Under The Hood Supabase Vectors 25:50 Admin UI Walkthrough 26:27 Managing Agent Workforce 26:49 Nanoclaw Security Containers 28:59 Telegram Agent Ops 30:32 Agent Personas Backstories 33:31 Thinking Hats Perspectives 37:25 Human Loop Guardrails 41:47 Marketing Distribution Channels 47:18 Factory Vision Rapid Launch 48:46 Wrap Up 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/ Skein: https://getskein.ai/ Beaker Stack website: https://beakerstack.com/ Beaker Stack GitHub: https://github.com/Artificer-Innovations/BeakerStack #techpodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #SaaS #Engineering #Development #BeakerStack #Skein #TechInnovation #AIRevolution #AIEngineering #AIAssistedCoding #AICoding #AIProgramming #AIAssistedProgramming

  • S2 · E25
    June 23 · 47 min

    AI and the Data Swamp In Your Backyard with Ben Wilcox

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub interview guest Ben Wilcox, CTO and CISO of ProArch, a Microsoft-focused data and AI system integrator. Wilcox describes his path into system integration, from cloud transformation and building managed security services, and now focused on helping customers adopt AI securely. The discussion centers on enterprise "data swamps," where unstructured, stale, and sensitive data create inaccurate AI outputs, and the new security risks as connectors make information easier to access. Wilcox argues organizations need stronger data governance, classification/labeling, segmentation, and purging, and should start with narrow, high-value AI use cases supported by cleaner data pipelines to improve accuracy and drive stakeholder buy-in. The hosts debate whether AI truly hallucinates or if faulty answers come from poor data, and whether the need for guardrails is anything new. Wilcox ends the episode reminding listeners that they are not alone in managing complex data. 00:00 Cold Open 00:22 Meet the Guest 03:00 What System Integrators Do 06:44 Modern SI for AI 09:39 Enterprise Data Swamp 15:08 Governance and Classification 17:41 Getting Budget Buy In 21:21 Bad Data vs Hallucinations 23:23 Bad Data Slows Everyone 24:43 Bronze Silver Gold Layers 26:53 Selling Data Debt Fixes 28:30 Scoped Copilot Show And Tell 31:04 AI Exposes Old Data Issues 33:11 Fusion Teams And Guardrails 37:00 Agents Need Real Controls 43:24 Defaults YOLO And Reviews 46:18 Wrap Up 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/ Ben Wilcox: https://www.linkedin.com/in/ben-wilcox/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #CISO #ProArch #Microsoft #SystemIntegration #AISecurity #DataSecurity #AI #DataSwamps #CloudTransformation #DataManagement #Cybersecurity #SystemIntegrators #Innovation #DataGovernance #CloudSolutions

  • S2 · E23
    June 16 · 44 min

    Pioneering Music Education with John von Seggern

    In this episode of "How Many CTOs Does It Take?" podcast, Brad Hefta-Gaub interviews John Von Seggern, founder/CEO/CTO of Future Proof Music School, about his shift from musician and online educator to building AI features using tools like Claude Code, n8n, and MCP servers. John describes the school's personalized learning approach using an AI chatbot "Cadence" integrated with student history and curriculum, hosted on LearnWorlds, and explains solving integration limits by creating an MCP server and scraping LearnWorlds pages into a mirror database for context. They discuss security and brittleness concerns with AI-built software, using audits and cross-checking between Codex and Claude, and how models enable refactoring. John outlines a hybrid org where human teachers handle advanced artistry via live workshops and mentoring, supported by an internal agent "Nova," and shares advice: state big goals upfront and have AI ask questions to clarify plans. The episode ends with a discussion on the future of AI generated music, and how AI can be a powerful tool for good. 00:00 Cold Open: People Still Matter 00:20 Meet John Von Seggern 02:40 From No Code to Claude 06:41 What The Platform Does 08:42 LMS Choice LearnWorlds 09:33 Context And RAG Logic 11:26 Building An MCP Server 12:16 Scraping For Lesson Data 16:02 Music Mindset For Systems 17:29 Vibe Coding Risks 20:14 Refactoring As Models Improve 22:49 Guardrails For Agents 23:13 Democratizing Code Limits 26:26 Supervising Agents Anywhere 28:39 Building Nova Business Brain 30:34 Hybrid School Team Setup 33:35 Advice: Ask 100 Questions 36:24 AI Music Future Debate 40:53 Look On The Bright Side, Closing Thoughts 43:22 Wrap Up And Credits Resources: How Many CTOs Pod: https://howmanyctospod.com Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/ John von Seggern: https://www.linkedin.com/in/johnvon/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #MusicEducation #TechInnovation #AIinEducation #Entrepreneurship #FutureProof #MusicTech #AIRevolution #MusicIndustry #Innovation

  • S2 · E22
    June 9 · 41 min

    Removing Bottlenecks, Not People with Stephanie Sylvestre

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad is joined by guest Stephanie Sylvestre, founder of AvatarBuddy, an AI company started 10 years ago to help people be the best version of themselves. Sylvestre argues for "AI plus human" rather than job elimination, and tells the story of how AvatarBuddy evolved from early research and prototypes to joining the OpenAI developer community in 2021, using teenagers for requirements and testing, and adopting curated "data vault" approaches (RAG) to improve results. AvatarBuddy provides managed AI-as-a-service, building and managing AI agents and advising clients, with tight controls on configuration. Sylvestre discusses her consulting process of AI opportunity mapping to identify root bottlenecks, with examples like reducing email overload by capturing requirements, creating digital twins for executive review, accelerating marketing work, and shortening month-end close, while warning that AI built without software engineering understanding can amplify security risks. The episode ends by affirming how AI not only allows for efficiency, but support for unique working styles that boosts morale. 00:00 Cold Open 00:34 Meet Stephanie 00:53 AI Before It Was Cool 03:04 Choosing AI Over VR 04:40 AvatarBuddy Origin Story 05:37 Early Prototypes and Testing 07:34 OpenAI Access and Launch 09:41 Data Vault Approach 10:33 What AvatarBuddy Does 11:48 AI Configuration Risks 12:11 Why AI Needs Software Basics 16:53 How Engagements Start 17:54 Opportunity Mapping Session 19:11 Prepared vs Unprepared Clients 22:38 CEO Bottleneck Twin 24:10 Blank Page Productivity 27:31 Scaling With Automation 28:57 Measurable Process Gains 32:10 Service Plus Product 32:57 IP As Differentiator 35:14 Personalized Agents Moat 39:37 Work Your Own Way 40:23 Find Stephanie Online 41:13 Podcast Wrap Up Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/ Stephanie Sylvestre: https://www.linkedin.com/in/stephanie-a-sylvestre/ Avatar Buddy: https://avatarbuddy.ai #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #Automation #FutureOfWork #AvatarBuddy #EliminateBottlenecks #AI #AIAssistedProgramming #AIRevolution #AIAndBusiness #AIAdvisory #BusinessOptimization #RemoveBottlenecksNotPeople #AIInsights

  • S2 · E21
    June 2 · 33 min

    Pioneer or Perish: How and When to Evolve Your Engineering Org Toward the AI Development Life Cycle

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss a high-performing engineering team that has effectively cleared its product backlog while using AI heavily, including a senior engineer who surprised Brad by running agents overnight to automatically perform fast, high-quality GitHub PR code reviews via a webhook-driven harness. The engineer built an opinionated, RAG-backed "world-class code review" skill set that pulls new PRs from selected repos, reviews them with defined criteria, and posts comments, highlighting the need to articulate engineering judgment rather than relying on gut feel. They explore how models and agent frameworks are becoming commoditized, making the key differentiator the ability to assemble components and codify professional, reusable skills. The conversation turns to how teams should integrate AI into the SDLC, balancing experimentation with a shared, periodically updated "long-term support" approach and quality gates, plus examples like agents generating test coverage and proposing fixes for failing tests. 00:00 Cold OPen 00:25 Podcast Intro And Banter 01:09 Mind Blown By AI Team 03:25 Overnight Agent Code Reviews 06:02 Make Your Opinions Clear 09:05 Models Vs Frameworks 12:32 Standardizing Team AI Use 14:43 LTS For Agent Workflows 15:51 Automate Repeated Tasks 21:52 SDLC First AI Second 25:04 Quality Gates And Automation 28:27 Agents For Tests And Bugs 30:55 Future Of Engineering Taste 32:40 Wrap Up 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 #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #EngineeringExcellence #AIInnovation #TechInnovation #FutureOfWork #AIDriven #AIAssistedProgramming #AIAssistedCoding #AIProgramming #AICoding #SDLC #ADLC

  • S2 · E20
    May 27 · 43 min

    Navigating the Future: Gas Town and Bespoke AI Agents

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss Brad's viral LinkedIn post arguing that AI has collapsed the economics that drove generalized SaaS, enabling more bespoke software for underserved SMBs and vertical niches. They debate practical examples like a plumber-specific CRM versus highly custom workflows for a regional law firm, including concerns about long-term maintenance, fragmentation, and risk. Brad contrasts "overnight magic" agent claims with what he sees in fractional CTO work: teams using AI within disciplined engineering practices and quality gates to deliver far more output, though not fully autonomous "dark factories" yet. They explore Scott's hands-on Gas Town workshop experience building a fantasy football app with multiple agents, noting orchestration value, tooling immaturity, resource constraints, and confusing nomenclature. The episode ends with why experienced operators still dismiss AI for production code and whether agent frameworks will be custom-built or marketplace-driven. 00:00 Cold Open 00:14 Show Intro and Hosts 00:58 Viral LinkedIn Post Read 03:28 "Agree... Sort Of" Nuance 04:40 Plumber CRM Example 08:36 Law Firm Workflow Doubts 11:37 Engineering Reality Check 14:29 Gas Town Workshop Demo 17:34 Factory Setup and Risks 20:28 Why Leaders Still Doubt AI 22:26 AI Naysayers 24:10 Massive PRs 27:42 Monorepo Momentum 29:07 Engineering Joy 31:10 AI Mistakes 33:19 Agent Personas 37:04 Agent Marketplace 38:54 K Shaped Future 41:15 Trust But Verify 42:30 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 #AIRevolution #AIAgents #AIAssistedCoding #AIAssisstedProgramming #BespokeSoftware #GasTown #TechInnovation #FutureTech #DigitalTransformation #TechLeadership #CTOInsights #TechTrends

  • S2 · E19
    May 19 · 52 min

    Uncovering Hidden Ambiguities: Why Product Managers Need to Adapt to AI Tooling

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss spec-driven development and SpecKit, starting with Brad's story of a product owner resisted SpecKit because it produced "too many words," alongside Scott's example of accepting a 60,000-line pull request by reviewing the spec instead of the code. They reflect on how product owners often can't define what they want until they see it, and how software work is usually clarified through ongoing back-and-forth dialogue. SpecKit surfaces hidden ambiguity by generating questions product owners hadn't considered, changing what used to become ad hoc decisions, bugs, or debt. They argue speed enables tighter iteration, but also pressures product to "know what they want," raising job-impact fears for engineers and possibly product managers too. Their conversation prompts ideas for training, collaborative workflows, and even self-design—tempered by the continued need for standardization and cross-functional expertise. The episode ends with the hosts reflecting on buisness ideas that never came to pass, and affirming that now value comes down to how well the problem can be described. 00:00 Cold Open 01:18 Product Is The Hard Part 02:26 Fast Teams Meet Specs 04:34 Too Many Words Pushback 05:10 Review The Spec Not Code 08:00 Coder To Reviewer Shift 10:20 Why POs Avoid Specificity 13:01 Surfacing Ambiguity Shock 17:43 Two Hour Sprint Loop 19:35 Jobs Changing Anxiety 23:39 Problem Versus Solution Trap 25:56 Vibe Tools And Self Design 26:49 Real Estate CRM Anecdote 28:28 AI Rewrites Software Economics 29:31 Self Design Simple Specs 31:00 When Standards Matter 32:23 Training Product Owners 36:05 Jobs Converge Under AI 37:49 Three Pane Spec IDE 40:40 AI Comes For PMs 44:29 Founder Moats And Copies 46:24 Missed Spotify Moment 48:19 RealNetworks Almost Made YouTube 51:36 Wrap Up 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 #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #SpecKit #SpecDrivenDevelopment #ProductManagement #AI #ProductOwners #CodeReview #QualityGates #IterativeProcess #UserStories #AIAssistedCoding #Spec

  • S2 · E18
    May 12 · 51 min

    A Fundamental Shift: Change Management, Psychological Safety, and AI's Impact on Engineering Leadership with Dr. Adam Link

    In this episode of "How Many CTOs Does It Take?" podcast, host Brad Hefta-Gaub is joined by Dr. Adam Link, former senior engineering manager at Coinbase, who shares his background leading global teams through highly technical transformations in fintech and crypto, including major infrastructure migrations. They discuss whether different kinds of change require different leadership approaches, emphasizing that change management is fundamentally about people. They discuss how fear makes change harder, so leaders must create psychological safety by providing "air cover" and managing messaging up and down. Adam notes that good managers must handle hard conversations like layoffs and performance issues with empathy while recognizing these outcomes aren't always personal decisions. He offers advice for engineers moving into management, including a tongue-in-cheek analogy that managers "test in production," and describes a challenging EC2-to-Kubernetes migration where success required strong technical credibility, hands-on help, and attention to team psychology. Adam and Brad compare blameless vs egoless retrospectives, discuss leaders defending engineers behind the scenes, and highlight the need for real remediation like error budgets or vendor changes. The conversation closes on AI as a fundamental industry shift, debate over the loss of hand-crafted coding vs enduring need for problem understanding, concerns about the junior-to-senior pipeline if entry roles disappear, decision fatigue from AI agents, and optimism about smaller teams producing better products with fewer bugs. 00:00 Cold Open 00:31 Podcast Intro Guest 02:24 Change Management Basics 03:49 Defining "Air Cover" 06:50 Hard People Decisions 10:19 Managers Test In Prod 13:38 Big Cloud Migration 17:34 Hands On Migration Help 21:04 Failure Friendly Culture 23:41 Blameless vs Egoless Retros Debate 28:56 Managing Up After Outages 30:19 Accountability And Error Budgets 31:38 Vendor Failures And Remediation 33:53 AI Adoption And Resistance 34:44 Craft Versus Assembly Line 37:52 AI As Mid Level Engineer 41:17 Business Value For Juniors 45:11 Pipeline And Decision Fatigue 47:15 Specs Waterfall Meets Agile 49:07 Summary And Closing Thoughts Resources: How Many CTOs Pod: https://howmanyctospod.com Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/ Dr. Adam Link: https://www.linkedin.com/in/adamlink/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AIRevolution #EngineeringCulture #ChangeManagement #LeadershipSkills #AIAssistedProgramming #AI #FinTech #Crypto #

  • S2 · E17
    May 5 · 47 min

    An Ideal Partnership: How and When to Split CTO and VP of Engineering Duties

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss the recurring question: when it's appropriate to hire a VP of Engineering and how to divide responsibilities so the CTO can better align product, business, and technology strategy. They define CTO vs VP of Engineering work, review Gemini's matrix (strategy/vision vs execution/people/process, external vs internal, success metrics, and typical direct reports), and add nuance about internal stakeholders within and outside the company. They discuss cases where leaders can't do both jobs and why founders shouldn't give the CTO title too early. They emphasize CTO/VPE as a yin-yang partnership with clear decision rights and KPIs. Brad shares experiences with split dev/ops teams and argues for engineers having operational skin in the game, while Scott outlines his org functions and defines ops as what's required to keep systems running. They propose carving up responsibilities by strategy vs building (and operating), debate punting corporate IT to the CFO versus keeping it tied to security, and consider using Gemini to suggest how to split roles. The episode closes on letting go of ego through clear expectations, Scott's recommendation of the book "First, Break All the Rules," how skill or interest gaps can force a split despite hierarchical titles, and a pro tip to align on expectations with your CEO so teams can measure progress and celebrate wins like uptime and cycle-time improvements. 00:00 Cold Open 00:27 Podcast Intro Banter 00:49 Small Business AI Win 02:09 Team Size Context 03:52 When to Add VPE 05:40 CTO vs VPE Roles 07:11 Gemini Comparison Matrix 10:54 Startup Hiring Patterns 13:39 Titles and Founder Pitfalls 15:18 Yin and Yang Partnership 18:09 Carving the Org Pie 20:31 Corporate IT and Security 24:20 Strategy Versus Execution 25:28 Reliability And SRE Ownership 27:24 Defining Operations Teams 30:04 On Call And Skin In Game 31:18 Using Gemini To Split Roles 33:08 Letting Go And Ego 34:33 KPIs Enable Delegation 37:28 Manager Clarity Framework 38:57 When Skill Gaps Force Split 41:55 Set Your Scorecard 44:16 Celebrate KPI Wins 45:51 Wrap Up 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 #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #VPofEngineering #Gemini #CTOvsVPE #VPE #SecurityMindset #AI #DevOps #GrowthMindset #TeamCollaboration #CorporateCulture #BusinessGrowth #AIIntegration #Operations #StrategicVision #ManagementStyles #RoleDivision #ExecutiveDecisions

  • S2 · E16
    April 28 · 40 min

    Where Does the Alpha Flow?: Rethinking Software Value in the Age of AI

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss a conversation Scott had with coworkers after discovering Confluence connected to Google Drive and Slack, raising questions about whether to rely on tools like Confluence or a generic layer like Claude to aggregate knowledge and enable agents. A colleague suggested "alpha flows to where building happens," prompting Scott to question whether he agrees, what engineers actually need from AI (clear specifications), and whether customer insights and business needs matter more than internal documents. The hosts explore different types of builders, how clean data becomes a differentiator once tooling is ubiquitous, and define "dirty" or stale data through examples of conflicting documentation and misleading dashboards. Brad argues that as the building gets easier, the value shifts to market understanding and especially to the spec, not the code, while both conclude that ultimately, advantage comes from strong guardrails for correctness and value. 00:00 Cold Open 00:26 Podcast Setup And Topic 00:52 Confluence AI Discovery 02:32 Alpha Flows To Builders 03:51 Six Big Questions 07:36 Long View On Differentiation 09:12 Specs And Translation Layer 13:15 Design Levels And Personas 17:24 Moats Disappear In AI Era 20:41 Security And Exploit Agents 21:54 Mythos And Free Code 22:33 Specifying What Matters 23:23 Agent Strip Mining Products 24:42 Dirty Data In Knowledge 28:30 Stale Docs And Deletion 30:31 Bias And Interpretation 32:08 Ready Aim Shoot Debate 34:49 Specs QA And Guardrails 37:30 Where Value Really Flows 39:29 Wrap Up And Subscribe 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 #AITransformation #DataDriven #Innovation #Automation #DisruptiveTechnology #AIFuture #AITrends #InnovationInAI #AIForBusiness #TechRevolution #AIInsights #AIRevolution #EthicalAI #AIAssistedCoding

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