How Many CTOs

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

In this bonus episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub dive into a conversation with Greg Conklin, exploring his experiences at two hypergrowth companies, Groupon and Dropbox. Greg shares insights on the unique cultural and technical strategies employed at both organizations during their rapid expansion phases. He discusses the challenges of technical debt, team building approaches, and the differing priorities at Groupon's distributed startup-like model versus Dropbox's cohesive, security-focused architecture. The episode also touches upon the role of senior engineering leadership in managing technical debt and optimizing engineering velocity across diverse teams.

• 00:00 Introduction: The Journey of Tech Debt
• 00:22 Exploring Hypergrowth at Dropbox and Groupon
• 01:25 Building Teams and Strategies
• 03:24 Cultural Differences and Technical Challenges
• 04:36 Platform and Ops Teams at Groupon vs Dropbox
• 07:41 Managing Technical Debt and Engineering Leadership
• 10:23 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/
• Greg Conklin: https://www.linkedin.com/in/gregoryconklin/
• Greg's Blog: https://gregconklin.com/

#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 #HyperGrowthEngineering #ScalingTech #PlatformEngineering #TechnicalStrategy #TechScalability #DistributedTeams #RapidGrowth #TechOrgDesign #GlobalEngineering #TechOps #AcquisitionStrategy #MultiTenantArchitecture #VelocityVsQuality #TechTradeoffs #EngineeringVelocity #SystemDesign #APILayer #InfrastructureStrategy #SaaSScaling

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub are joined by special guest Greg Conklin for a candid and insightful conversation on what it takes to build high-performing engineering teams.

Drawing from their shared time at the telemedicine startup 98point6, the trio unpacks hard-earned lessons around tech debt, operational excellence, and culture-first leadership. Topics include:

• Why setting guardrails for quality, performance, and reliability early pays dividends later.
• The real value of postmortems and RCA meetings (and how to make them stick).
• How overly strong culture filters can unintentionally suppress bravery and dissent.
• What startups should prioritize in their first few quarters to avoid painful rework.

Whether you're scaling an early-stage team or trying to fix systemic issues in a mature org, this episode delivers practical frameworks and honest reflection from leaders who've been there.

• 00:00 Introduction and Welcome
• 00:46 Guest Introduction: Greg Conklin
• 02:05 Revisiting 98.6: Lessons Learned
• 03:27 Empowerment and Quality at 98.6
• 05:32 Challenges in Engineering Management
• 10:46 Operational Excellence and Technical Debt
• 24:25 Dropbox Postmortem Insights
• 27:14 Blameless vs. Egoless Retrospectives
• 30:51 Setting Early Standards in Startups
• 35:11 Challenges in Test Automation
• 38:49 Local Development and Ephemeral Environments
• 44:33 Concluding Thoughts on Engineering Leadership
• 47:15 Podcast 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/
• Greg Conklin: https://www.linkedin.com/in/gregoryconklin/
• Greg's Blog: https://gregconklin.com/

#TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #EngineeringProductivity #TeamVelocity #DevCulture #TeamCulture #EngineeringCulture #Retrospectives #BlamelessRetrospectives #EgolessRetrospective #Agile #ContinuousImprovement #RootCauseAnalysis #FiveWhys #IncidentResponse #GrowthMindset #TeamTrust #BuildingTrust #SDLC #TechDebt #OperationalExcellence #Postmortems #SiteReliability #SLA #SystemReliability #IncidentManagement #EngineeringCultureMatters #EmpoweredTeams #EngineeringGuardrails #PsychologicalSafety #DevProcess #EngineeringStandards #ShiftLeft #StartupLeadership #EngineeringMaturity #ScalingEngineering #EngineeringOrgDesign #ProductEngineeringAlignment #CI_CD #DevEx #TestAutomation #Observability #BuildPipeline #LocalDevEnvironment

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub explore the art and impact of retrospectives in engineering teams. Drawing on their experiences in both software and high-stakes environments like mountain rescue, they discuss the value of retrospectives for continuous improvement, building trust, and uncovering root causes of both successes and failures. The conversation covers practical frameworks for running retros, the importance of psychological safety, and the challenges of accountability and follow-through. They also debate the strengths and limitations of the "five whys" technique and share real-world anecdotes about incident response, team culture, and the unique dynamics of remote work.

• 00:00 Introduction and Banter
• 00:28 Cocktails, Bathtub Drinks, and Whiskey
• 01:40 Welcome to the Episode: Retrospectives
• 02:05 Retrospectives in Agile and Mountain Rescue
• 04:11 The Overlap Between Debriefs in Rescue and Software
• 04:30 Core Values: "Get Better Every Day"
• 04:50 Growth Mindset and Team Improvement
• 05:00 Retros for Every Error?
• 06:40 The Value of Interrogating Successes
• 08:40 Types of Retrospectives: Sprint, Project, Incident
• 09:30 Practical Framework for Sprint Retros
• 14:25 Accountability and Tracking Retro Action Items
• 18:05 Handling Big, Complex Retro Outcomes
• 18:40 Real-World Example: Staging Environments and Edge Cases
• 21:40 Tech Debt, Investment, and Team Process
• 23:40 Building Trust for Effective Retros
• 25:43 Incident Retros: Blameless vs. Egoless
• 27:15 Tone, Timeline, Five Whys, and Root Cause Analysis
• 32:00 The Role of Incident Commander
• 33:15 The Five Whys
• 34:10 The Challenge of Branching Root Causes
• 37:44 Working Agreements, Action Items, and Continuous Improvement
• 39:14 Retros and a Culture of Trust
• 40:04 Building Trust on Remote Teams
• 41:14 Call to Action 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 #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #EngineeringProductivity #TeamVelocity #DevCulture #TeamCulture #EngineeringCulture #Retrospectives #BlamelessRetrospectives #EgolessRetrospective #Agile #ContinuousImprovement #RootCauseAnalysis #FiveWhys #IncidentResponse #GrowthMindset #TeamTrust #BuildingTrust #SDLC

In this bonus episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub sit down once again with technologist and philosopher John Helm, this time for a wide-ranging conversation about artificial intelligence, epistemology, and what it means to be human in an age of machines. John draws on his background in statistics and philosophy to frame AI through the lens of knowledge, reasoning, and moral agency.

The episode touches on the hype and promise of modern AI systems, explores the difference between correlation and understanding, and raises deep questions about consciousness, ethics, and whether general intelligence can exist without emotion. John even challenges the language we use to describe AI by grounding the conversation in ancient philosophical questions, the structure of scientific truth, and how humans conceptualize value and meaning.

• 00:00 Introduction: What Makes Us, Us
• 00:19 Diving into AI: Hype and Reality
• 01:03 Philosophical Insights: Knowledge and Understanding
• 03:00 AI and Human Understanding: Patterns and Predictions
• 05:19 Ethical Concerns and Human Morality
• 08:14 Concluding Thoughts: Ethics, Knowledge, and Governance
• 10:28 Outro: Follow 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/
• John Helm: https://www.linkedin.com/in/johnlhelm/

#TechPodcast #EngineeringPodcast #PodcastForDevs #HowManyCtos #Podcast #Ctos #Technology #Leadership #EngineeringLeadership #CtoPodcast #ArtificialIntelligence #AGI #MachineLearning #AIHypeCycle #AIPhilosophy #EthicsInAI #MoralMachines #ReasoningModels #Epistemology #KnowledgeAndTruth #HumanConsciousness #AIAndHumanity #GeneralIntelligence #CorrelationVsCausation #AIAlignment #PredictiveModels #PhilosophyOfAI

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub welcome guest John Helm to discuss the complexities and ramifications of technical debt within software projects. The conversation explores various analogies, including financial bonds and naked calls, to explain the impact of technical debt on project timelines and functionality. John offers insights on measuring technical debt, its human aspects, and strategies for managing complexity in software systems. The episode highlights the importance of defining technical debt, communicating its impact to business stakeholders, and finding a balance in software development to avoid costly delays and incomplete features.

• 00:00 Introduction and Guest Welcome
• 02:06 Defining Tech Debt
• 04:50 The Human Element in Tech Debt
• 07:28 Financial Analogies and Tech Debt
• 21:42 Complexity and Dependencies
• 29:54 The Challenge of Refactoring Complexity
• 31:12 Defining and Addressing Technical Debt
• 33:44 The Risks of Over-Decoupling
• 37:55 Considering Technical Bankruptcy
• 43:16 Balancing Technical Debt and Developer Satisfaction
• 51:11 Exploring Technical Debt Metrics
• 53:19 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/
• John Helm: https://www.linkedin.com/in/johnlhelm/
• SPACE Developer Productivity: https://dl.acm.org/doi/pdf/10.1145/3454122.3454124
• OMG Automated Technical Debt Measure: https://www.omg.org/spec/ATDM/1.0/About-ATDM

#TechPodcast #EngineeringPodcast #PodcastForDevs #HowManyCtos #Podcast #Ctos #TechnicalDebt #TechDebt #MeasuringTechDebt #SoftwareArchitecture #EngineeringLeadership #CtoPodcast #PlatformEngineering #SoftwareMaintenance #Refactoring #LegacyCode #HumanFactors #BehavioralEconomics #DecisionMaking #StakeholderCommunication #RiskManagement #OriginalMistakes #SecondSystemEffect #BondModel #NakedCalls #TechnicalBankruptcy #EngineeringProductivity #TeamHealth #SpaceMetrics #DoraMetrics #ContinuousImprovement #DeferredMaintenance

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss the intricate challenges of engineering leadership, focusing on the decomposition of monolithic software systems and the monumental task of managing tech debt. They delve into the practical strategies for breaking down monoliths, the complexity of interdependencies and 'God objects,' and debate the merits of incremental rewrites versus complete overhauls. The conversation highlights the need for continuous investment in system maintenance and the struggle to measure the tangible benefits of these efforts. They explore metrics like DORA and the difficulty in aligning business stakeholders with long-term, patient refactoring initiatives. This episode provides valuable insights into effectively handling legacy codebases and advocating for engineering investments.

• 00:00 Introduction and Podcast Setup
• 00:47 Key Challenges in Engineering
• 01:40 Decomposing the Monolith
• 04:10 Strategies for Incremental Improvement
• 06:12 Real-World Examples and Challenges
• 18:31 Measuring Engineering Productivity
• 21:54 The Challenge of Consistent Processes
• 23:25 Estimation Accuracy as a Key Metric
• 25:58 The Complexity of Measuring Value
• 30:44 The Financial Argument for Maintenance
• 36:41 Declaring Technical Debt Bankruptcy
• 42:41 Concluding Thoughts 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 #Technology #Leadership #Ctos #TechnicalDebt #Management #ProblemSolvingTechniques #ProblemSolvingStrategies #Engineering #Entrepreneurship #EngineeringManagement #Monoliths #Microservices #Dora #SoftwareArchitecture #MonolithToMicroservices #DecomposeTheMonolith #BallOfMud #GodObjects #LegacyCode #Refactoring #EngineeringProductivity #PlatformEngineering #CtoPodcast #EngineeringLeadership #ScalingEngineering #TeamVelocity #CycleTime #DoraMetrics #TechnicalStrategy #BuildVsRewrite #DevCulture #CleanCode #SoftwareMaintenance #ContinuousImprovement #DeferredMaintenance #YakShaving #OctopusObjects #InboxBankruptcy #ReplaceTheBoat #PrometheusShip #ShipOfTheseus

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub are joined by Kevin Goldsmith, a seasoned tech leader with a background in both music and technology. Kevin shares insights from his early career in the music industry, his journey through various tech roles, and his book 'It Depends'. The discussion covers important topics like learning from failure, managing tech debt, and the impact of AI-assisted coding. Kevin also talks about the value of retrospectives, even after successful projects, and shares experiences from his tenure at Spotify. As a fun bonus Brad and Kevin both discuss their histories as record label owners and conclude by recommending some of their new favorite music.

• 00:00 Introduction and Guest Welcome
• 00:55 Record Label Stories
• 02:42 Kevin's Career Journey
• 07:34 Writing 'It Depends'
• 13:19 Lessons from Failure
• 18:04 Spotify Retrospectives
• 25:02 Feature Requests and Fun Stories
• 27:42 Exploring Music Algorithms
• 28:36 Technical Challenges and Business Implications
• 29:23 The Social Aspect of Music Sharing
• 31:29 Managing Multiple Spotify Accounts
• 33:00 Tackling Tech Debt in Monolithic Systems
• 42:23 AI Assisted Coding: A Tool for the Future
• 48:40 Music Recommendations and Closing Remarks

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/
• Kevin Goldsmith: https://www.linkedin.com/in/goldsmith/
• It Depends Book: https://itdependsbook.net/
• Tacocat: http://tacocatdotcom.com/
• The Telescreens: https://linktr.ee/Telescreens

#podcast #technology #leadership #ctos #technicaldebt #management #leadership #problemsolvingtechniques #problemsolvingstrategies #engineering #entrepreneurship #engineeringmanagement #retrospectivs #ai #aiassistedcoding #punkrock