How Many CTOs
By Brad Hefta-Gaub & Scott Porad
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Image by Brad Hefta-Gaub & Scott Porad
Category: Technology
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Episodes: 72
Description
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
| Episode | Date |
|---|---|
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Pioneer or Perish: How and When to Evolve Your Engineering Org Toward the AI Development Life Cycle
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Jun 02, 2026 |
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Navigating the Future: Gas Town and Bespoke AI Agents
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May 27, 2026 |
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Uncovering Hidden Ambiguities: Why Product Managers Need to Adapt to AI Tooling
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May 19, 2026 |
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A Fundamental Shift: Change Management, Psychological Safety, and AI's Impact on Engineering Leadership with Dr. Adam Link
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May 12, 2026 |
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An Ideal Partnership: How and When to Split CTO and VP of Engineering Duties
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May 05, 2026 |
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Where Does the Alpha Flow?: Rethinking Software Value in the Age of AI
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Apr 28, 2026 |
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Product-Market Fit and Pragmatic AI: Insight from RevenueCat's CTO Miguel Carranza
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Apr 21, 2026 |
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The Most Optimized Blue: Differences Between UI and User Experience Design with Nick Cawthon
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Apr 14, 2026 |
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Balancing Innovation and Safety: CTOs Check-In About AI Evolution
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Apr 07, 2026 |
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Engaging Employees in Security Appreciation with Robert Siciliano
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Mar 31, 2026 |
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Building Trust with AI: David Espindola on the Path Forward
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Mar 24, 2026 |
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Beyond Transcripts: Language Nuances and Audio Signals with Carter Huffman of Modulate
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Mar 17, 2026 |
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Introducing the ADLC: The Agent Development Life Cycle
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Mar 10, 2026 |
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The Evolving Role of Tech Leadership with Philip Rosedale
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Mar 03, 2026 |
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Predictions and Reflections: One Year Anniversary of the How Many CTOs Does It Take? Podcast
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Feb 24, 2026 |
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Adapt or Fade: Interviewing for Developers in the Age of AI Assisted Coding
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Feb 17, 2026 |
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From Rave Promoter to SaaS Innovator: Revolutionizing Event Management with Ritesh Patel
|
Feb 10, 2026 |
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From the Dress Code to the Bottom Line: A CTO Business Primer
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Feb 03, 2026 |
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The K-Shape of AI Development: Managing Digital Interns
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Jan 27, 2026 |
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Setting the Tone: Building Trust Through Security
|
Jan 20, 2026 |
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Rediscovering the Joy of Coding through AI with Paul Brown
|
Jan 13, 2026 |
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Year In Review: How Many CTOs Does It Take To Finish A Season?
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Dec 23, 2025 |
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Turtles All The Way Down: AI Insights with Scott W. Bradley
|
Dec 16, 2025 |
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The AI Race: Who's Ahead, Anthropic or OpenAI?
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Dec 09, 2025 |
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CTO Therapy: The Risks and Rewards of Vendor Partnerships
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Dec 02, 2025 |
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Let Them Eat Tokens: AI Efficiency vs. Global Good
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Nov 25, 2025 |
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Cabinet Doors Should Open: Avoiding Assumptions in Product Requirements
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Nov 18, 2025 |
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The State of AI in 2025: What the DORA Report Reveals
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Nov 11, 2025 |
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The AI Hype Cycle: Navigating Growth and Skepticism
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Nov 04, 2025 |
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In Search of the Exceptional: Unpacking the Traits of 10x Engineers
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Oct 28, 2025 |
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The Documented SDLC: Why Every Team Needs One (and When)
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Oct 21, 2025 |
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Navigating BADD vs. FaDD: Strategic Refactoring in Software Development
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Oct 14, 2025 |
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From Specs to Monitoring: A CTO's Guide to QA Best Practices
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Oct 07, 2025 |
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Deploys, Demos, and the Elusive Metric of Engineering Productivity
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Sep 30, 2025 |
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Product Debt: The Hidden Drag on Innovation
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Sep 23, 2025 |
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From Streaker Apps to AI Safety Loopholes: What CTOs Need to Know
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Sep 16, 2025 |
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Do Engineering Managers Need to Code? Leveling, Calibration & Craft
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Sep 10, 2025 |
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From Prompts to Product: How AI is Changing Software Development
|
Sep 02, 2025 |
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From Bugs to Bloat: Product Debt, KPIs, and the Cost of Features
|
Aug 26, 2025 |
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CTO Therapy: Managing Urgency, Expectations, and Trust
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Aug 19, 2025 |
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From Coldplay to Code: AI Wins, Data Lakes, and the Age-Old Centralized vs. Distributed Debate
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Aug 12, 2025 |
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Design in the Age of AI: Craft, Tools, and the Future of Creativity
|
Aug 05, 2025 |
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Storytelling, Not Spin: Founder-Led Marketing with Dan Woods
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Jul 29, 2025 |
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The Outsourcing Playbook Gets an AI Rewrite: Engineering in the Age of AI and Global Teams
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Jul 22, 2025 |
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From Code to Careers: AI's Disruption of Software and Work Itself
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Jul 15, 2025 |
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How GenAI Is Changing the Two Guys in a Garage Founder Story
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Jul 08, 2025 |
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Autonomous Engineering Teams: What Works, What Breaks
|
Jul 01, 2025 |
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The End of Programming As We Know It? Justin Kaufman's tips on building fast with AI
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Jun 26, 2025 |
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From Chicken to Chatbots: Generative AI in Hospitality with Justin Kaufman
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Jun 24, 2025 |
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Fake Profiles, Real Disruption: What AI Is (and Isn't) Doing to Tech Recruiting with Dave Hardwick
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Jun 19, 2025 |
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Beyond the Resume: How to Hire and Get Hired in Tech with Dave Hardwick
|
Jun 17, 2025 |
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Bonus Episode with Greg Conklin: Navigating Hyper-growth and Tech Debt at Groupon and Dropbox
|
Jun 12, 2025 |
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Culture, Quality, and Tech Debt: Lessons from the Front Lines with Greg Conklin
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Jun 10, 2025 |
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Lessons from the Mountains: Retrospectives and the Secret Sauce of High Performance Teams
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Jun 03, 2025 |
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Exploring AI, Knowledge, and Ethics with John Helm (Bonus Episode)
|
May 29, 2025 |
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Understanding and Managing Technical Debt: Insights from John Helm
|
May 27, 2025 |
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The Ball of Mud - Tackling Software Monoliths and Decomposing Tech Debt: Strategies and Challenges
|
May 20, 2025 |
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Embracing Failure and Innovation: Lessons from Punk Rock with Kevin Goldsmith
|
May 13, 2025 |
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Navigating Technical Debt and Code Quality in Agile Teams
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May 06, 2025 |
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The Reality of AI in Software Engineering and the Future of Work
|
Apr 29, 2025 |
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Tackling Tech Culture and Interviewing: Insights from Ted Neward
|
Apr 22, 2025 |
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The Power of Drafting Implementation Plans: Insights and Strategies
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Apr 15, 2025 |
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Learning Styles and Team Dynamics: A Journey from Personal Trips to Strategic Decisions
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Apr 08, 2025 |
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Bonus Episode: Challenges and Insights From Using Cursor to Add a Feature to Our Website
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Apr 03, 2025 |
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Embracing AI in Software Development: An Interview with Michael Natkin of Glowforge
|
Apr 01, 2025 |
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Org Structures and Measuring Platform Team Success
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Mar 25, 2025 |
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Effective Staff Meetings: Balancing Structure and Flexibility
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Mar 18, 2025 |
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Building Trust and Authentic Connections in Remote Teams
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Mar 12, 2025 |
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Embracing Innovation: Introducing the PR FAQ Framework with Marcelo Calbucci
|
Mar 04, 2025 |
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Measuring Technical Debt and Technical Investments
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Feb 19, 2025 |
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Introducing Our Hosts: Scott and Brad
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Feb 19, 2025 |
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Introduction to How Many CTOs Does It Take? Podcast
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Feb 19, 2025 |