How Many CTOs?

Scott Porad

Co-host

Scott is a technology executive and co-host of How Many CTOs? He has led engineering and product organizations through growth, turnarounds, and platform shifts, and is especially interested in how leaders build culture that actually scales.

Episodes with Scott

All episodes →
S2E40 Preparing for the Worst: Tabletop Exercises, Unit Tests, and Everything In Between Brad & Scott Oct 13, 2026
44:51
S2E39 Understanding The Fear: Adaptive Leadership in the AI Age Brad & Scott Oct 6, 2026
34:28
S2E37 Managing Skepticism: Balancing Tradition and Technology with AI Brad & Scott Sep 22, 2026
49:59
S2E36 From Academia to Industry: Scott Hanson on the Future of AI and Edge Computing with Scott Hanson, Ambiq Sep 15, 2026
45:58
S2E35 Beyond Cost Reduction: AI in Revenue Generation and Innovation with Andy Boettcher with Andy Boettcher, DoubleTrack Sep 8, 2026
50:24
S2E34 The Hardware/Software Blend: Visionary Innovations in Health Tech with Eyebot's Jack Moldave with Jack Moldave, Eyebot Sep 1, 2026
52:47
S2E33 Fast, On Time, or Fully Utilized? Choosing What to Optimize in Engineering Delivery Brad & Scott Aug 25, 2026
16:37
S2E32 The Pace of Innovation: Systems Thinking for Faster Engineering Brad & Scott Aug 18, 2026
56:48
S2E31 Method to the Madness: A CTO Framework for Systemic AI Adoption Brad & Scott Aug 11, 2026
45:26
S2E30 There's A Pattern To Follow: An Interview with Robert "Uncle Bob" Martin Brad & Scott Aug 4, 2026
01:01:57
S2E29 Is Uncle Bob Right? Reading Code vs. Architecting the Future Brad & Scott Jul 28, 2026
43:05
S2E28 Token Maxxing and Local Inference: Navigating the Shift in AI Usage for Developers Brad & Scott Jul 21, 2026
01:00:30
S2E27 This Has Always Been A Problem: Slot Machine Devs and Growing Junior Engineers in the Age of AI Brad & Scott Jul 14, 2026
56:26
S2E25 Introducing Skein and Beaker Stack: Using AI Agent Engineers to Ship SaaS Faster Brad & Scott Jun 30, 2026
49:54
S2E24 AI and the Data Swamp In Your Backyard with Ben Wilcox with Ben Wilcox, ProArch Jun 23, 2026
47:33
S2E22 Removing Bottlenecks, Not People with Stephanie Sylvestre with Stephanie Sylvestre, AvatarBuddy Jun 9, 2026
41:46
S2E21 Pioneer or Perish: How and When to Evolve Your Engineering Org Toward the AI Development Life Cycle Brad & Scott Jun 2, 2026
33:24
S2E20 Navigating the Future: Gas Town and Bespoke AI Agents Brad & Scott May 27, 2026
43:21
S2E19 Uncovering Hidden Ambiguities: Why Product Managers Need to Adapt to AI Tooling Brad & Scott May 19, 2026
52:37
S2E17 An Ideal Partnership: How and When to Split CTO and VP of Engineering Duties Brad & Scott May 5, 2026
47:02
S2E16 Where Does the Alpha Flow?: Rethinking Software Value in the Age of AI Brad & Scott Apr 28, 2026
40:30
S2E15 Product-Market Fit and Pragmatic AI: Insight from RevenueCat's CTO Miguel Carranza with Miguel Carranza, RevenueCat Apr 21, 2026
48:48
S2E14 The Most Optimized Blue: Differences Between UI and User Experience Design with Nick Cawthon with Nick Cawthon, gauge.io Apr 14, 2026
48:24
S2E13 Balancing Innovation and Safety: CTOs Check-In About AI Evolution Brad & Scott Apr 7, 2026
32:06
S2E11 Building Trust with AI: David Espindola on the Path Forward Scott Mar 24, 2026
40:09
S2E10 Beyond Transcripts: Language Nuances and Audio Signals with Carter Huffman of Modulate with Carter Huffman, Modulate AI Mar 17, 2026
41:29
S2E9 Introducing the ADLC: The Agent Development Life Cycle Brad & Scott Mar 10, 2026
44:18
S2E7 Predictions and Reflections: One Year Anniversary of the How Many CTOs Does It Take? Podcast Brad & Scott Feb 24, 2026
43:59
S2E6 Adapt or Fade: Interviewing for Developers in the Age of AI Assisted Coding Brad & Scott Feb 17, 2026
30:47
S2E5 From Rave Promoter to SaaS Innovator: Revolutionizing Event Management with Ritesh Patel with Ritesh Patel, Ticket Fairy Feb 10, 2026
49:10
S2E4 From the Dress Code to the Bottom Line: A CTO Business Primer Brad & Scott Feb 3, 2026
32:07
S2E3 The K-Shape of AI Development: Managing Digital Interns Brad & Scott Jan 27, 2026
39:08
S2E2 Setting the Tone: Building Trust Through Security Brad & Scott Jan 20, 2026
53:52
S2E1 Rediscovering the Joy of Coding through AI with Paul Brown with Paul Brown Jan 13, 2026
43:19
S1E49 Year In Review: How Many CTOs Does It Take To Finish A Season? Brad & Scott Dec 23, 2025
12:58
S1E48 Turtles All The Way Down: AI Insights with Scott W. Bradley Brad & Scott Dec 16, 2025
59:37
S1E47 The AI Race: Who's Ahead, Anthropic or OpenAI? Brad & Scott Dec 9, 2025
25:05
S1E46 CTO Therapy: The Risks and Rewards of Vendor Partnerships Brad & Scott Dec 2, 2025
41:56
S1E45 Let Them Eat Tokens: AI Efficiency vs. Global Good Brad & Scott Nov 25, 2025
40:36
S1E44 Cabinet Doors Should Open: Avoiding Assumptions in Product Requirements Brad & Scott Nov 18, 2025
33:02
S1E43 The State of AI in 2025: What the DORA Report Reveals Brad & Scott Nov 11, 2025
38:15
S1E42 The AI Hype Cycle: Navigating Growth and Skepticism Brad & Scott Nov 4, 2025
30:12
S1E41 In Search of the Exceptional: Unpacking the Traits of 10x Engineers Brad & Scott Oct 28, 2025
45:18
S1E40 The Documented SDLC: Why Every Team Needs One (and When) Brad & Scott Oct 21, 2025
57:51
S1E39 Navigating BADD vs. FaDD: Strategic Refactoring in Software Development Brad & Scott Oct 14, 2025
37:19
S1E38 From Specs to Monitoring: A CTO's Guide to QA Best Practices Brad & Scott Oct 7, 2025
39:54
S1E37 Deploys, Demos, and the Elusive Metric of Engineering Productivity Brad & Scott Sep 30, 2025
51:51
S1E36 Product Debt: The Hidden Drag on Innovation Brad & Scott Sep 23, 2025
34:43
S1E35 From Streaker Apps to AI Safety Loopholes: What CTOs Need to Know Brad & Scott Sep 16, 2025
40:32
S1E34 Do Engineering Managers Need to Code? Leveling, Calibration & Craft Brad & Scott Sep 10, 2025
39:06
S1E33 From Prompts to Product: How AI is Changing Software Development Brad & Scott Sep 2, 2025
35:26
S1E32 From Bugs to Bloat: Product Debt, KPIs, and the Cost of Features Brad & Scott Aug 26, 2025
28:39
S1E31 CTO Therapy: Managing Urgency, Expectations, and Trust Brad & Scott Aug 19, 2025
56:57
S1E30 From Coldplay to Code: AI Wins, Data Lakes, and the Age-Old Centralized vs. Distributed Debate Brad & Scott Aug 12, 2025
54:46
S1E29 Design in the Age of AI: Craft, Tools, and the Future of Creativity Brad & Scott Aug 5, 2025
55:30
S1E28 Storytelling, Not Spin: Founder-Led Marketing with Dan Woods with Dan Woods Jul 29, 2025
51:14
S1E27 The Outsourcing Playbook Gets an AI Rewrite: Engineering in the Age of AI and Global Teams Brad & Scott Jul 22, 2025
24:36
S1E26 From Code to Careers: AI's Disruption of Software and Work Itself Brad & Scott Jul 15, 2025
53:02
S1E25 How GenAI Is Changing the Two Guys in a Garage Founder Story Brad & Scott Jul 8, 2025
52:31
S1E24 Autonomous Engineering Teams: What Works, What Breaks Brad & Scott Jul 1, 2025
50:31
S1E23 The End of Programming As We Know It? Justin Kaufman's tips on building fast with AI Brad & Scott Jun 26, 2025
16:50
S1E22 From Chicken to Chatbots: Generative AI in Hospitality with Justin Kaufman with Justin Kaufman, Mount Joy Jun 24, 2025
01:02:26
S1E21 Fake Profiles, Real Disruption: What AI Is (and Isn't) Doing to Tech Recruiting with Dave Hardwick with Dave Hardwick Jun 19, 2025
10:56
S1E20 Beyond the Resume: How to Hire and Get Hired in Tech with Dave Hardwick with Dave Hardwick Jun 17, 2025
41:35
S1E19 Bonus Episode with Greg Conklin: Navigating Hyper-growth and Tech Debt at Groupon and Dropbox with Greg Conklin Jun 12, 2025
11:11
S1E18 Culture, Quality, and Tech Debt: Lessons from the Front Lines with Greg Conklin with Greg Conklin Jun 10, 2025
47:51
S1E17 Lessons from the Mountains: Retrospectives and the Secret Sauce of High Performance Teams Brad & Scott Jun 3, 2025
42:11
S1E16 Exploring AI, Knowledge, and Ethics with John Helm (Bonus Episode) Brad & Scott May 29, 2025
11:04
S1E15 Understanding and Managing Technical Debt: Insights from John Helm Brad & Scott May 27, 2025
54:36
S1E14 The Ball of Mud - Tackling Software Monoliths and Decomposing Tech Debt: Strategies and Challenges Brad & Scott May 20, 2025
43:32
S1E13 Embracing Failure and Innovation: Lessons from Punk Rock with Kevin Goldsmith with Kevin Goldsmith May 13, 2025
52:05
S1E12 Navigating Technical Debt and Code Quality in Agile Teams Brad & Scott May 6, 2025
16:43
S1E11 The Reality of AI in Software Engineering and the Future of Work Brad & Scott Apr 29, 2025
21:07
S1E10 Tackling Tech Culture and Interviewing: Insights from Ted Neward Brad & Scott Apr 22, 2025
50:28
S1E9 The Power of Drafting Implementation Plans: Insights and Strategies Brad & Scott Apr 15, 2025
24:09
S1E8 Learning Styles and Team Dynamics: A Journey from Personal Trips to Strategic Decisions Brad & Scott Apr 8, 2025
28:31
S1E7 Bonus Episode: Challenges and Insights From Using Cursor to Add a Feature to Our Website Brad & Scott Apr 3, 2025
12:49
S1E6 Embracing AI in Software Development: An Interview with Michael Natkin of Glowforge with Michael Natkin Apr 1, 2025
45:19
S1E5 Org Structures and Measuring Platform Team Success Brad & Scott Mar 25, 2025
53:40
S1E4 Effective Staff Meetings: Balancing Structure and Flexibility Brad & Scott Mar 18, 2025
14:57
S1E3 Building Trust and Authentic Connections in Remote Teams Brad & Scott Mar 12, 2025
37:20
S1E2 Embracing Innovation: Introducing the PR FAQ Framework with Marcelo Calbucci with Marcelo Calbucci Mar 4, 2025
40:31
S1E1 Measuring Technical Debt and Technical Investments Brad & Scott Feb 19, 2025
33:48
Episode 2 Introducing Our Hosts: Scott and Brad Brad & Scott Feb 19, 2025
38:27
Episode 1 Introduction to How Many CTOs Does It Take? Podcast Brad & Scott Feb 19, 2025
11:08