Career Path to CTO
Paths into the CTO seat: skills beyond code, leadership transitions, and advice for aspiring technology executives.
Episodes
- Preparing for the Worst: Tabletop Exercises, Unit Tests, and Everything In Between
TaskRabbit's overnight AWS region migration from us-west-1 to us-west-2, describing the months of preparation, detailed runbook, large war-room call,…
- Understanding The Fear: Adaptive Leadership in the AI Age
Growing fear about AI among engineers and managers, framing it as an "adaptive moment" requiring leaders to disrupt old stabilizing practices. They…
- Simplifying Tech Through Empathy and Understanding with Frank Bravo
Is joined by guest Frank Bravo, a Bay Area technologist who spent 30 years as CTO in local media, helping put a newspaper's full editorial content online…
- Managing Skepticism: Balancing Tradition and Technology with AI
How AI is changing software engineering referencing Kent Beck's idea that AI makes much existing knowledge less useful while making a smaller portion far…
- From Academia to Industry: Scott Hanson on the Future of AI and Edge Computing
Scott Hanson, founder and CTO of Ambiq, a company focused on ultra-low-power chips for "intelligence everywhere," with 300M+ units shipped into wearables…
- Beyond Cost Reduction: AI in Revenue Generation and Innovation with Andy Boettcher
Andy Boettcher, Chief Innovator of DoubleTrack, a boutique data and AI consultancy. Andy recounts his 33 years across systems, development, with 13 years…
- The Hardware/Software Blend: Visionary Innovations in Health Tech with Eyebot's Jack Moldave
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…
- Fast, On Time, or Fully Utilized? Choosing What to Optimize in Engineering Delivery
A leadership conversation where three senior stakeholders wanted different outcomes from engineering: delivering faster, maximizing utilization, or…
- The Pace of Innovation: Systems Thinking for Faster Engineering
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…
- Method to the Madness: A CTO Framework for Systemic AI Adoption
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…
- There's A Pattern To Follow: An Interview with Robert "Uncle Bob" Martin
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…
- Is Uncle Bob Right? Reading Code vs. Architecting the Future
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…
- Token Maxxing and Local Inference: Navigating the Shift in AI Usage for Developers
Token spending and the "token maxing" backlash, sparked by a GitHub Copilot budget issue and broader industry moves to optimize tokens. The hosts argues…
- This Has Always Been A Problem: Slot Machine Devs and Growing Junior Engineers in the Age of AI
How managing armies of coding agents can be physically draining, likening it to context switching in flat organizations. Scott references Yuval Harari's…
- From Chaos to Control: Bringing Specification Driven Design to Vibe Coding with David Bauer
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…
- 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…
- AI and the Data Swamp In Your Backyard with Ben Wilcox
Guest Ben Wilcox, CTO and CISO of ProArch, a Microsoft-focused data and AI system integrator. Wilcox describes his path into system integration, from…
- Pioneering Music Education with John von Seggern
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…
- Removing Bottlenecks, Not People with Stephanie Sylvestre
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.…
- Pioneer or Perish: How and When to Evolve Your Engineering Org Toward the AI Development Life Cycle
A high-performing engineering team that has effectively cleared its product backlog while using AI heavily, including a senior engineer who surprised Brad…
- Navigating the Future: Gas Town and Bespoke AI Agents
Brad's viral LinkedIn post arguing that AI has collapsed the economics that drove generalized SaaS, enabling more bespoke software for underserved SMBs…
- Uncovering Hidden Ambiguities: Why Product Managers Need to Adapt to AI Tooling
Spec-driven development and SpecKit, starting with Brad's story of a product owner resisted SpecKit because it produced "too many words," alongside…
- A Fundamental Shift: Change Management, Psychological Safety, and AI's Impact on Engineering Leadership with Dr. Adam Link
Is joined by Dr. Adam Link, former senior engineering manager at Coinbase, who shares his background leading global teams through highly technical…
- An Ideal Partnership: How and When to Split CTO and VP of Engineering Duties
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,…
- Where Does the Alpha Flow?: Rethinking Software Value in the Age of AI
A conversation Scott had with coworkers after discovering Confluence connected to Google Drive and Slack, raising questions about whether to rely on tools…
- Product-Market Fit and Pragmatic AI: Insight from RevenueCat's CTO Miguel Carranza
" interview Miguel Carranza Spanish-born co-founder/CTO of RevenueCat, who describes discovering subscription billing pain while building the Elevate app…
- The Most Optimized Blue: Differences Between UI and User Experience Design with Nick Cawthon
Talk with Nick Cawthon of gauge.io, who shares highlights from RSA 2026 and his career designing UX for InfoSec/SecOps/DevOps tools. Nick argues that…
- Balancing Innovation and Safety: CTOs Check-In About AI Evolution
In this "What's on your mind?" episode of the "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss how non-engineers using…
- Engaging Employees in Security Appreciation with Robert Siciliano
Welcomes Boston-raised security speaker Robert Siciliano, who traces his path into security from early experiences with crime, teaching physical…
- Building Trust with AI: David Espindola on the Path Forward
I n this episode of "How Many CTOs Does It Take?" podcast, Scott Porad hosts solo and interviews technologist David Espindola about AI. Espindola explains…
- Beyond Transcripts: Language Nuances and Audio Signals with Carter Huffman of Modulate
Talk with Carter Huffman, CTO and co-founder of Modulate AI, about his path from machine learning work at NASA's Jet Propulsion Lab to building voice AI…
- Introducing the ADLC: The Agent Development Life Cycle
" open with Super Bowl reactions and a meme about non-fans describing plays, then pivot to the ai.com halftime ad, where heavy spending reportedly led to…
- The Evolving Role of Tech Leadership with Philip Rosedale
Brad Hefta-Gaub is joined by guest co-host Philip Rosedale to explore the multifaceted role of a CTO, comparing it with the CEO position. They discuss the…
- Predictions and Reflections: One Year Anniversary of the How Many CTOs Does It Take? Podcast
" reflect on the first year of the podcast's publication, discussing Scott's ongoing questions about tech debt and struggles with refactoring, the…
- Adapt or Fade: Interviewing for Developers in the Age of AI Assisted Coding
The evolving landscape of interviewing for programmer positions in the age of AI-assisted coding. They discuss the relevance of traditional leetcode…
- From Rave Promoter to SaaS Innovator: Revolutionizing Event Management with Ritesh Patel
Sit down with Ritesh Patel, co-founder of Ticket Fairy . Ritesh shares his journey from coding and organizing raves to creating a powerful vertical SaaS…
- From the Dress Code to the Bottom Line: A CTO Business Primer
The interplay between tech and business. Starting with comments about their own scruffiness and stories of wearing hats to interviews and fancy…
- The K-Shape of AI Development: Managing Digital Interns
Yet again delve into the transformative impact of AI on software engineering. Brad shares his 2025 Cursor Year in Review, revealing his record 2.9 billion…
- Setting the Tone: Building Trust Through Security
The role of CTOs in setting a security-minded culture and provide real-life anecdotes of security breaches and incidents. The conversation covers critical…
- Rediscovering the Joy of Coding through AI with Paul Brown
Hosts Scott Porad and Brad Hefta-Gaub are joined by Paul Brown to delve into the misplaced fears of AI supplanting engineers, highlighting instead its…
- Year In Review: How Many CTOs Does It Take To Finish A Season?
In this special public service announcement episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub announce that they…
- Turtles All The Way Down: AI Insights with Scott W. Bradley
Guest Scott W. Bradley, Managing Partner at Facet Digital, to delve into the complexities and potential pitfalls of AI technology. With insights drawn…
- The AI Race: Who's Ahead, Anthropic or OpenAI?
Compare Anthropic and OpenAI's distinct business strategies. While OpenAI takes a high-risk, expansive approach aiming for rapid growth, Anthropic focuses…
- CTO Therapy: The Risks and Rewards of Vendor Partnerships
Delve into Scott's recent meeting with AWS. They discuss the concept of vendors supporting their clients, weighing potential benefits against risks like…
- Let Them Eat Tokens: AI Efficiency vs. Global Good
Dive into the pervasive influence of AI, starting with a critical look at Apple's Siri and its struggles to keep up with competitors like ChatGPT. They…
- Cabinet Doors Should Open: Avoiding Assumptions in Product Requirements
The critical importance of clear requirements in both hardware and software projects. Using the analogy of a home renovation project, they explore how…
- The State of AI in 2025: What the DORA Report Reveals
Dive into the 2025 DORA Metrics Report on the state of AI-assisted software development. They discuss key findings such as the near-universal adoption of…
- The AI Hype Cycle: Navigating Growth and Skepticism
Reflect on the recent shifts in Big Tech's approach to AI, discussing the changing perceptions and economic impacts of the technology. They provide…
- In Search of the Exceptional: Unpacking the Traits of 10x Engineers
Dive deep into the concept of the 10x engineer—those rare developers who are exponentially more productive than their peers. They discuss attributes such…
- The Documented SDLC: Why Every Team Needs One (and When)
Start with a quick retrospective, or is it an encore, of recent rock concerts before stage-diving into a lively discussion about the Software Development…
- Navigating BADD vs. FaDD: Strategic Refactoring in Software Development
Dive deep into the engineering crossroads between Better Architecture Driven Development (BADD) and Feature Driven Development (FaDD) . They unpack the…
- From Specs to Monitoring: A CTO's Guide to QA Best Practices
Tackle the evolving landscape of quality assurance in web apps . They challenge the notion of QA as just "manual testers at the end," instead framing…
- Deploys, Demos, and the Elusive Metric of Engineering Productivity
Wrestle with one of the industry's toughest questions: How do you measure engineering productivity? The conversation explores the hypothesis that deploy…
- Product Debt: The Hidden Drag on Innovation
Dive into the concept of product debt : what it is, how it differs from technical debt, and why it matters. They unpack how hidden or forgotten product…
- From Streaker Apps to AI Safety Loopholes: What CTOs Need to Know
Break down the quirky and serious sides of today's AI. They cover vibe coding, smart glasses, debugging with ChatGPT, and the big question of whether AI…
- Do Engineering Managers Need to Code? Leveling, Calibration & Craft
Delve into the art and science of engineering leveling frameworks. From performance reviews to competency guides, they explore how organizations can…
- From Prompts to Product: How AI is Changing Software Development
The evolving reality of AI productivity, and what it means for software engineering, product management, and the future of work. They kick things off with…
- From Bugs to Bloat: Product Debt, KPIs, and the Cost of Features
Dig into the messy reality of product management effectiveness, and what happens when bugs reveal deeper product debt. They kick things off with a…
- CTO Therapy: Managing Urgency, Expectations, and Trust
Delve into the critical issue of building a sense of urgency and trust within engineering teams. They discuss the importance of schedule accuracy,…
- From Coldplay to Code: AI Wins, Data Lakes, and the Age-Old Centralized vs. Distributed Debate
In this "Summer Catch-Up" episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub swap stories from the field, covering…
- Storytelling, Not Spin: Founder-Led Marketing with Dan Woods
Are joined by Dan Woods, an expert in founder-led marketing. Dan shares his extensive experience in helping software engineers and product management…
- The Outsourcing Playbook Gets an AI Rewrite: Engineering in the Age of AI and Global Teams
Dig deep into the real-world lessons of managing outsourced and distributed engineering teams. Drawing on decades of experience with partners in Romania,…
- From Code to Careers: AI's Disruption of Software and Work Itself
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…
- How GenAI Is Changing the Two Guys in a Garage Founder Story
Tech entrepreneurs and avid scuba divers Justin Wolf and Joe Malek to share the story behind their generative AI–powered scuba guidebook and community…
- Autonomous Engineering Teams: What Works, What Breaks
Unpack one of the most debated questions in engineering leadership: Should engineering managers also serve as tech leads? They explore the organizational…
- From Chicken to Chatbots: Generative AI in Hospitality with Justin Kaufman
Special guest Justin Kaufman . Justin discusses his unique journey from working in health tech to founding the Mount Joy restaurant, where he's…
- Fake Profiles, Real Disruption: What AI Is (and Isn't) Doing to Tech Recruiting with Dave Hardwick
With Dave Hardwick, the disruptive yet beneficial impact of AI on recruitment processes. They explore how AI tools are revolutionizing candidate searches…
- Beyond the Resume: How to Hire and Get Hired in Tech with Dave Hardwick
Dave Hardwick, a seasoned technical recruiter. Together, they explore the intricacies of recruiting engineering talent, the gaps between what CTOs think…
- Bonus Episode with Greg Conklin: Navigating Hyper-growth and Tech Debt at Groupon and Dropbox
Dive into a conversation with Greg Conklin, exploring his experiences at two hypergrowth companies, Groupon and Dropbox. Greg shares insights on the…
- Culture, Quality, and Tech Debt: Lessons from the Front Lines with Greg Conklin
Are joined by special guest Greg Conklin for a candid and insightful conversation on what it takes to build high-performing engineering teams. Drawing…
- Lessons from the Mountains: Retrospectives and the Secret Sauce of High Performance Teams
The art and impact of retrospectives in engineering teams. Drawing on their experiences in both software and high-stakes environments like mountain…
- Exploring AI, Knowledge, and Ethics with John Helm (Bonus Episode)
Sit down once again with technologist and philosopher John Helm, this time for a wide-ranging conversation about artificial intelligence, epistemology,…
- Understanding and Managing Technical Debt: Insights from John Helm
Guest John Helm to discuss the complexities and ramifications of technical debt within software projects. The conversation explores various analogies,…
- The Ball of Mud - Tackling Software Monoliths and Decomposing Tech Debt: Strategies and Challenges
The intricate challenges of engineering leadership, focusing on the decomposition of monolithic software systems and the monumental task of managing tech…
Articles
- How should developers prepare for interviews in the age of AI-assisted coding?
- What are the best practices for conducting technical interviews with AI-assisted coding?
- How can system integrators help businesses transition to AI and cloud platforms?
- How is AI being integrated into software development processes?
- How is AI transforming the tools used by tech recruiters?
- What are the key differences between a CTO and a VP of Engineering in a software company?
- What challenges do fake profiles pose in tech recruiting?
- What is the debate between centralized and distributed data teams?