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

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub dig deep into the real-world lessons of managing outsourced and distributed engineering teams. Drawing on decades of experience with partners in Romania, India, Syria, and Ukraine, they unpack what makes these relationships thrive, or fail.

From timezone pains and cultural mismatches to the power of long-term trust and shared context, Scott and Brad cover the spectrum of challenges leaders face when their teams span the globe. They share tips for CTOs navigating fractional teams, staff augmentation models, and agency partnerships, and reflect on how the rise of generative AI is starting to echo some of the same tensions and tradeoffs seen in outsourcing.

If you're building a product with engineers you don't see in the same room, or considering whether AI is the next evolution of outsourcing, this conversation is a must-listen.

• 00:00 Introduction: The Need for Communication in Distributed Teams
• 01:04 Challenges of Outsourcing: Pros and Cons
• 01:24 Personal Experiences with Outsourcing
• 02:00 Successful Outsourcing Strategies
• 02:35 Long-term Commitments and Time Zone Issues
• 03:33 Staff Augmentation and Agency Experiences
• 06:32 Fractional CTO Insights and Common Issues
• 19:06 The Importance of Shared Understanding
• 21:21 The Role of Product Management and Technical Leadership
• 22:24 Future of Outsourcing and AI Integration
• 23:39 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 #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #GenAI #AIRevolution #AIEngineer #BuildWithAI #GenerativeAI #StartupTech #RemoteTeams #OutsourcingStrategy #DistributedEngineering #EngineeringManagement #StartupTech #FractionalCTO #TeamVelocity #EngineeringCulture #BuildWithAI #GenerativeAI #AIAndOutsourcing #GlobalTeams #TimeZoneChallenges #ScalingEngineering #TechLeadership #OffshoreEngineering #AgencyWork #Nearshoring

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub dive into the fast-evolving world of generative AI—and what it means for the future of software development, careers, and the economy at large.

They unpack how tools like GPT-4o and Claude are shifting the very nature of programming work, boosting productivity while raising deeper questions about the future of white-collar jobs. From the rise of AI-assisted coding to ethical concerns around climate impact and military use, Scott and Brad cover the technical, social, and philosophical stakes of this moment.

They also explore whether a future with fewer human coders could spark bigger societal changes—like universal basic income—and make the case for why adaptability, critical thinking, and a willingness to learn new tools are the keys to surviving (and thriving) in this new AI-powered landscape.

• 00:00 Introduction and Greetings
• 00:27 Discussing AI and Augmented Programming
• 03:20 AI's Impact on Productivity and Society
• 04:23 Climate Impact and Future Concerns
• 05:01 AI in Healthcare and Other Applications
• 08:08 The Future of Software Development
• 15:40 Generative AI and Personal Projects
• 24:59 Advice for the Next Generation
• 27:46 The Challenge of Staying Current
• 28:33 Specialization vs. Generalization
• 28:47 The Role of AI in Specialized Jobs
• 30:20 Navigating the Rapid Tech Changes
• 31:31 Optimizing AI Collaboration
• 33:19 Understanding the Cynefin Framework
• 35:01 Complex vs. Complicated Systems
• 39:46 AI's Impact on Software Engineering
• 41:55 The Future of QA and Testing
• 44:33 Preparing for an AI-Driven Future
• 49:27 The Debate on Universal Basic Income
• 51:29 Concluding Thoughts and Ethical Questions
• 52:26 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/
• Why using ChatGPT is not bad for the environment - a cheat sheet: https://andymasley.substack.com/p/a-cheat-sheet-for-conversations-about
• Cynefin Framework: https://en.wikipedia.org/wiki/Cynefin_framework

#TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #GenAI #AIRevolution #AIEngineer #BuildWithAI #GenerativeAI #StartupTech #ClaudeAI #GPT4o #OpenAI #AIProductivity #LLMTools #AIEngineering #FutureOfWork #AgenticAI #AIAgents #AIInStartups #CTOInsights #SoftwareDevelopment #AIUpdate #TechStrategy #FastMovingTech

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub welcome tech entrepreneurs and avid scuba divers Justin Wolf and Joe Malek to share the story behind their generative AI–powered scuba guidebook and community app. What started as a side project became a test case for building fast with LLMs and pushing the boundaries of what small, technical founding teams can accomplish.

The conversation dives deep into the reality of building with GenAI: the tools, the tradeoffs, and the surprising limitations. Along the way, they explore philosophical questions about human creativity, AI collaboration, and how founders might rethink MVPs, product-market fit, and even team size in this new era. From fighter jets and PACT tests to the Wall Street Journal's AI film experiment, this wide-ranging conversation connects code, culture, and curiosity in a way only How Many CTOs can.

• 00:00 Introduction and Welcome
• 00:36 Meet the Guests: Justin Wolf and Joe Malick
• 02:10 The Birth of a Scuba Diving App
• 03:22 Challenges and Solutions in App Development
• 06:27 Generative AI: A Double-Edged Sword
• 14:15 Technical Insights and AI Tools
• 21:29 Future Plans and Testing
• 26:43 The Importance of Control in Development
• 27:10 Automated Testing and PACT Tests
• 28:23 Wall Street Journal's AI Film Experiment
• 30:15 AI's Limitations and Human Creativity
• 32:06 AI in Fighter Jets: Human vs. Machine
• 33:55 The Future of AI and Human Intelligence
• 42:35 Generative AI and the Future of Work
• 47:12 The Role of Marketers in the Age of AI
• 50:18 Final Thoughts and Inspirations

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/
• Justin Wolf: https://www.linkedin.com/in/justinjwolf/
• Joe Malek: https://www.linkedin.com/in/jomalek/

#TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #StartupTech #GenAI #Founders #SoloFounder #TwoGuysInAGarage #GenerativeAI #AIProductivity #StartupJourney #AIForStartups #LLM #FoundingWithAI #MVPStrategy #EarlyStageStartups #StartupLife #AIRevolution #FutureOfFounding #AIEngineer #BuildWithAI #FounderTools #TechInnovation #FromGarageToGPT

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub unpack one of the most debated questions in engineering leadership: Should engineering managers also serve as tech leads? They explore the organizational signals that indicate whether a team is ready to thrive with true cross-functional autonomy, and what can go wrong when roles and responsibilities blur. And of course, it wouldn't be a How Many CTOs episode without a dive into AI-assisted coding—Scott and Brad share some recent wins (and fails) using tools like ChatGPT Codex.

• 00:00 Introduction and Host Greetings
• 00:53 Generative AI Tools Discussion
• 01:41 Challenges with AI and Coding
• 05:07 Onboarding New Engineers
• 10:03 Engineering Management Structures
• 25:02 Identifying Team Anti-Patterns
• 25:45 The Role of Psychological Safety
• 26:30 Product Manager's Influence
• 27:07 Balancing Centers of Gravity
• 27:59 Importance of a Tech Lead
• 28:37 Risks of Siloed Teams
• 32:14 Tech Lead vs. Engineering Manager
• 39:09 Prerequisites for Cross-Functional Teams
• 47:34 Core Beliefs and Team Structure
• 48:54 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/
• Mindsets That Shape Software Delivery Team Structures - https://medium.com/@rethinkyourunderstanding/mindsets-that-shape-software-delivery-team-structures-51d25f20638c

#TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #EngineeringProductivity #TeamVelocity #DevCulture #TeamCulture #EngineeringCulture #EngineeringManager #TechLead #ProductEngineering #OrgDesign #TeamStructure #TechLeadership #PeopleManagement #EngineeringCulture #StartupLeadership #EMvsTL #TeamDynamics #LeadershipTradeoffs #ScalingEngineering #OrgRoles #CollaborationMatters #ManagementVsLeadership

In this bonus episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub engage in a deep and insightful conversation with their guest Justin Kaufman about the transformative role of AI in software development. The discussion explores the potential of AI to revolutionize the industry by automating aspects of coding and problem-solving, potentially reducing the need for traditional software engineers in certain sectors. Justin shares his optimistic yet realistic views on how AI can significantly boost developer productivity and highlights real-world examples of AI-driven improvements in test coverage and coding efficiency. The episode also delves into the significance of organizing codebases for better AI integration and the advantages of using GraphQL to facilitate AI operations within applications. The conversation underscores the evolving nature of software engineering roles and the importance of embracing AI to stay relevant and succeed in the tech industry.

• 00:00 Introduction and Setting the Stage
• 01:07 The Future of Software Programming Jobs
• 02:48 AI's Limitations and Human Creativity
• 07:23 Real-World AI Success Stories
• 09:33 Embracing AI for Career Growth
• 12:22 Technical Insights and Best Practices
• 16:09 Conclusion and Episode 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/
• Justin Kaufman: https://www.linkedin.com/in/justinkaufman/

#TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #AIEatsCode #SoftwareIsDead #WillAIBuildItBetter #EndOfProgramming #TechHotTakes #MonolithVsMicroservices #FastAndRecklessDev #AIShippedIt #GenerativeAI #BuildOrBeReplaced #StartupStack #FutureOfEngineering #HowManyCTOs #DumbSystemsSmartResults #GraphQL #TechProvocation #AISoftwareDevelopment #EngineeringDisruption #BuildFastDieYoung

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub interview special guest Justin Kaufman. Justin discusses his unique journey from working in health tech to founding the Mount Joy restaurant, where he's implemented innovative tech solutions to enhance customer engagement. The conversation covers topics such as AI-assisted coding, the benefits and challenges of monolithic architecture, and the future of customer relationship management through modern LLMs. Justin also shares anecdotes about his time working with both hosts, revealing different aspects of their management styles.

• 00:00 Introduction
• 00:48 Guest Introduction: Justin Kaufman
• 01:29 Justin's Prepared List of Topics
• 03:49 Justin's Journey: From Health Tech to Chicken Shack
• 06:14 Innovating the Restaurant Experience
• 08:56 Building a Custom POS System
• 14:20 Leveraging AI for Personalization
• 17:41 The Power of Small Teams and AI Tools
• 28:05 Engaging Customers with Interactive Games
• 33:15 Evolution of Chatbots and CRM
• 34:09 Expanding Beyond Restaurants
• 35:17 Technical Challenges and Solutions
• 36:24 Monolith vs. Microservices
• 45:38 Serverless Architecture and Tech Debt
• 49:55 The Future of Small Teams and AI
• 57:05 Reflections on Management Styles
• 01:01:27 Conclusion and Farewell

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/
• Justin Kaufman: https://www.linkedin.com/in/justinkaufman/

#TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #AI #LLM #OpenAI #ChatGPT #CRMSolutions #SmallBusinessTech #LangChain #RAG #AIEngineering #RealWorldAI #AIAgents #CustomGPTs #VectorDB #LLMStack #PromptEngineering #FullStackAI #AIInfra #AIUX #StartupEngineering #TechInnovation #AIForSMB #ChickenTech #GPTInTheWild #AppliedLLM #SemanticSearch #LocalBusinessTools

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss with Dave Hardwick, the disruptive yet beneficial impact of AI on recruitment processes. They explore how AI tools are revolutionizing candidate searches for recruiters, but also touch upon the challenge of encountering fake profiles. The conversation further delves into whether hiring managers are considering AI proficiency in candidates and how engineers can leverage AI to advance their careers. The episode emphasizes the importance of curiosity, critical thinking, and adaptability in navigating the evolving landscape of AI in technology roles.

• 00:00 Introduction: The Evolving Landscape of AI
• 00:34 AI's Impact on Recruitment Tools
• 01:53 Challenges with Fake Profiles
• 04:37 AI in Candidate Assessment
• 08:40 Future of AI in Recruitment
• 10:17 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/
• Dave Hardwick: https://www.linkedin.com/in/dave-hardwick-4596a0/

#TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #EngineeringProductivity #TeamVelocity #DevCulture #TeamCulture #EngineeringCulture #Agile #TechDebt #OperationalExcellence #EngineeringCultureMatters #EmpoweredTeams #DevProcess #StartupLeadership #EngineeringMaturity #ScalingEngineering #EngineeringOrgDesign #HyperGrowth #TechnicalRecruiting #HiringEngineers #RecruiterInsights #AIRecruiting #FakeProfiles #TechHiring #TalentSearch #AIinHiring #AIethics #CareerDevelopment #FutureOfWork #SoftwareCareers #EngineeringCareers #AIDisruption #RecruiterTips #InterviewingWithAI #AIReadiness

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub welcome Dave Hardwick, a seasoned technical recruiter. Together, they explore the intricacies of recruiting engineering talent, the gaps between what CTOs think they want and what they actually hire, and the importance of clear job descriptions and scorecards in the hiring process. Dave shares insights on what makes a strong resume, the challenges of hiring for senior technical roles, and the significance of soft skills like resourcefulness and leverage in startup environments. This episode is a deep dive into effective recruiting strategies for engineering teams.

• 00:00 Introduction to the Podcast
• 01:04 Meet Dave Hardwick: Technical Recruiter
• 01:34 The Art of Recruiting: Insights and Challenges
• 05:54 Effective Interviewing and Scorecards
• 13:08 Crafting the Perfect Resume
• 20:45 The Unassuming Engineer's Journey
• 24:16 Common Resume Mistakes
• 25:13 Hiring for Startups: Values and Flexibility
• 25:34 The Realities of Startup Life
• 30:21 Resourcefulness and Leverage in Startups
• 31:29 Intentionality in Startups
• 32:53 Evaluating Engineering Managers and Directors
• 38:08 The Executive Mindset
• 40:08 Conclusion and Contact Information

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/
• Dave Hardwick: https://www.linkedin.com/in/dave-hardwick-4596a0/

#TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #EngineeringProductivity #TeamVelocity #DevCulture #TeamCulture #EngineeringCulture #Agile #TechDebt #OperationalExcellence #EngineeringCultureMatters #EmpoweredTeams #DevProcess #StartupLeadership #EngineeringMaturity #ScalingEngineering #EngineeringOrgDesign #HyperGrowth #TechnicalRecruiting #HiringEngineers #EngineeringHiring #CTOHiring #RecruiterTips #ResumeAdvice #TechCareers #Scorecards #InterviewTips #StartupCulture #SoftSkillsMatter #TeamFit #HiringMistakes #StartupRecruiting #ExecutiveHiring