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 →S2E43
What Broke in Tech: Code Quality, AI Guardrails, and the Evolving Software Engineer
Brad & Scott
Brad & Scott continue to recap Gergely Orosz's "State of the Tech Industry" talk and focus on what "broke" and "what's next. " They argue that machine-generated code is overwhelming pull requests and code review, exposing that many organizations' quality gates were implicitly built around human speed, and they discuss how 98% uptime is becoming an unacceptable norm.
S2E42
The State of Tech in 2026: What Changed And What Didn't
Brad & Scott
Brad & Scott discuss a Pragmatic Engineer talk on the state of the tech industry in 2026, focusing on what changed and what hasn't. They argue this is a "golden age" of building software due to AI, while acknowledging current "creative destruction" that may ultimately make the industry leaner.
S2E41
The Human Needs in Augmented Coding: A Conversation with Kent Beck
with Kent Beck
Brad & Scott interview software pioneer Kent Beck about his background (JUnit, test-driven development, extreme programming, Agile Manifesto, and his book "Tidy First? ") and his current focus on "augmented development" with AI, which he calls a "genie.
S2E40
Preparing for the Worst: Tabletop Exercises, Unit Tests, and Everything In Between
Brad & Scott
Brad & Scott discuss 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, minor cleanup issues, and why periodic region moves can serve as valuable "hygiene" to relearn and document complex systems while advancing disaster recovery and business continuity. They then explain tabletop exercises as structured incident-response drills designed to uncover gaps in process and documentation, sharing scenario ideas like data deletion, token leaks, cloud outages, ransomware, and internal actors, including an embezzlement case where the perpetrator joined incident response.
S2E39
Understanding The Fear: Adaptive Leadership in the AI Age
Brad & Scott
Brad & Scott discuss growing fear about AI among engineers and managers, framing it as an "adaptive moment" requiring leaders to disrupt old stabilizing practices. They explore concerns that AI lowers the barrier for others to change systems, increasing accountability, on-call risk, and architectural drift—problems that existed pre-AI but are now intensified.
S2E37
Managing Skepticism: Balancing Tradition and Technology with AI
Brad & Scott
Brad & Scott discuss 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 more valuable. They describe teams collaborating through "cohorts" of AI agents for PR review and adversarial checking, and debate whether engineers will be evaluated on agent quality versus their ability to direct and manage agents like a driver or jockey.
S2E36
From Academia to Industry: Scott Hanson on the Future of AI and Edge Computing
with Scott Hanson, Ambiq
Brad & Scott interview Scott Hanson, founder and CTO of Ambiq, a company focused on ultra-low-power chips for "intelligence everywhere," with 300M+ units shipped into wearables and other devices. Hansen traces Ambiq's origins with University of Michigan smart-dust research and his PhD work on subthreshold computing—running transistors at extremely low voltages for quadratic energy savings—then explains the challenges of making it manufacturable across temperature and process variation.
S2E35
Beyond Cost Reduction: AI in Revenue Generation and Innovation with Andy Boettcher
with Andy Boettcher, DoubleTrack
Brad & Scott interview Andy Boettcher, Chief Innovator of DoubleTrack, a boutique data and AI consultancy. Andy recounts his 33 years across systems, development, with 13 years in Salesforce, and how his career shifted into data/AI full-time after ChatGPT's 2022 release.
S2E34
The Hardware/Software Blend: Visionary Innovations in Health Tech with Eyebot's Jack Moldave
with Jack Moldave, Eyebot
Brad & Scott interview 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 and prescriptions in retail settings. Jack explains Eyebot's kiosk experience in Walmart Vision Centers, including intake questions, visual acuity testing, touch-free refraction and glasses scanning, and remote review by licensed optometrists/ophthalmologists with prescriptions returned in under 15 minutes.
S2E33
Fast, On Time, or Fully Utilized? Choosing What to Optimize in Engineering Delivery
Brad & Scott
Brad & Scott discuss a leadership conversation where three senior stakeholders wanted different outcomes from engineering: delivering faster, maximizing utilization, or delivering on time—highlighting unclear norms and expectations in the software delivery system. The hosts argue you can't optimize all three at once, note that maximum utilization is a poor goal (systems perform better below 100% utilization), and debate prioritizing speed versus schedule.
S2E32
The Pace of Innovation: Systems Thinking for Faster Engineering
Brad & Scott
Brad & Scott 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 explore a meta-question: if non-engineering teams couldn't tell engineering to "go faster," what would they change to increase engineering throughput?
S2E31
Method to the Madness: A CTO Framework for Systemic AI Adoption
Brad & Scott
Brad & Scott discuss 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 hosts outline four intertwined AI workstreams: getting AI to handle increasingly complex engineering (from functions to features to systems), moving toward autonomous "dark factory" software development, scaling AI adoption through standards and systems (shifting from organic experimentation to systemic usage, like AI code review and possible security/architect review agents), and managing token spend, including discussion of token-maxing incentives, looping, and interest in local inference and vendor lock-in mitigations such as AWS Bedrock.
S2E30
There's A Pattern To Follow: An Interview with Robert "Uncle Bob" Martin
with Robert "Uncle Bob" Martin
Brad & Scott 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 C, C++, and Java, to now using AI agents to code. He explains how the Agile movement emerged from the design patterns community, Extreme Programming, and the 2001 Snowbird meeting that produced the Agile Manifesto.
S2E29
Is Uncle Bob Right? Reading Code vs. Architecting the Future
Brad & Scott
Brad & Scott discuss 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 produced by his programming agents. They unpack his argument that strong "control systems" like automated unit and end-to-end tests, static analysis, and architecture acceptance criteria can replace line-by-line review, shifting human attention to higher-level architecture and justification.
S2E28
Token Maxxing and Local Inference: Navigating the Shift in AI Usage for Developers
Brad & Scott
Brad & Scott discuss token spending and the "token maxing" backlash, sparked by a GitHub Copilot budget issue and broader industry moves to optimize tokens. The hosts argues companies should focus on value and learning rather than premature token optimization, while still adding circuit breakers to prevent runaway costs.
S2E27
This Has Always Been A Problem: Slot Machine Devs and Growing Junior Engineers in the Age of AI
Brad & Scott
Brad & Scott discuss how managing armies of coding agents can be physically draining, likening it to context switching in flat organizations. Scott references Yuval Harari's "Sapiens," connecting the cognitive and agricultural revolutions to modern pressures.
S2E25
Introducing Skein and Beaker Stack: Using AI Agent Engineers to Ship SaaS Faster
Brad & Scott
Brad & Scott discuss Brad's experiment proving that AI can dramatically boost output for teams with strong engineering practices. Brad shares an MIT-licensed open-source SaaS template called Beaker Stack, which includes web and mobile scaffolding, CI/CD for preview/staging/production, automated setup, observability, email tooling, and Stripe-based tiered billing with feature gating.
S2E24
AI and the Data Swamp In Your Backyard with Ben Wilcox
with Ben Wilcox, ProArch
Brad & Scott interview guest Ben Wilcox, CTO and CISO of ProArch, a Microsoft-focused data and AI system integrator. Wilcox describes his path into system integration, from cloud transformation and building managed security services, and now focused on helping customers adopt AI securely.
S2E22
Removing Bottlenecks, Not People with Stephanie Sylvestre
with Stephanie Sylvestre, AvatarBuddy
Scott 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. Sylvestre argues for "AI plus human" rather than job elimination, and tells the story of how AvatarBuddy evolved from early research and prototypes to joining the OpenAI developer community in 2021, using teenagers for requirements and testing, and adopting curated "data vault" approaches (RAG) to improve results.
S2E21
Pioneer or Perish: How and When to Evolve Your Engineering Org Toward the AI Development Life Cycle
Brad & Scott
Brad & Scott discuss a high-performing engineering team that has effectively cleared its product backlog while using AI heavily, including a senior engineer who surprised Brad by running agents overnight to automatically perform fast, high-quality GitHub PR code reviews via a webhook-driven harness. The engineer built an opinionated, RAG-backed "world-class code review" skill set that pulls new PRs from selected repos, reviews them with defined criteria, and posts comments, highlighting the need to articulate engineering judgment rather than relying on gut feel.
S2E20
Navigating the Future: Gas Town and Bespoke AI Agents
Brad & Scott
Brad & Scott discuss Brad's viral LinkedIn post arguing that AI has collapsed the economics that drove generalized SaaS, enabling more bespoke software for underserved SMBs and vertical niches. They debate practical examples like a plumber-specific CRM versus highly custom workflows for a regional law firm, including concerns about long-term maintenance, fragmentation, and risk.
S2E19
Uncovering Hidden Ambiguities: Why Product Managers Need to Adapt to AI Tooling
Brad & Scott
Brad & Scott discuss spec-driven development and SpecKit, starting with Brad's story of a product owner resisted SpecKit because it produced "too many words," alongside Scott's example of accepting a 60,000-line pull request by reviewing the spec instead of the code. They reflect on how product owners often can't define what they want until they see it, and how software work is usually clarified through ongoing back-and-forth dialogue.
S2E17
An Ideal Partnership: How and When to Split CTO and VP of Engineering Duties
Brad & Scott
Brad & Scott discuss 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, business, and technology strategy. They define CTO vs VP of Engineering work, review Gemini's matrix (strategy/vision vs execution/people/process, external vs internal, success metrics, and typical direct reports), and add nuance about internal stakeholders within and outside the company.
S2E16
Where Does the Alpha Flow?: Rethinking Software Value in the Age of AI
Brad & Scott
Brad & Scott discuss a conversation Scott had with coworkers after discovering Confluence connected to Google Drive and Slack, raising questions about whether to rely on tools like Confluence or a generic layer like Claude to aggregate knowledge and enable agents. A colleague suggested "alpha flows to where building happens," prompting Scott to question whether he agrees, what engineers actually need from AI (clear specifications), and whether customer insights and business needs matter more than internal documents.
S2E15
Product-Market Fit and Pragmatic AI: Insight from RevenueCat's CTO Miguel Carranza
with Miguel Carranza, RevenueCat
Brad & Scott " interview Miguel Carranza Spanish-born co-founder/CTO of RevenueCat, who describes discovering subscription billing pain while building the Elevate app and turning that hard, "boring" problem into a YC-backed business. He explains RevenueCat's scale (billions of API requests/day) and the resulting priorities: product-market fit, reliability/security, and sustaining culture in a fully remote team across 27 countries.
S2E14
The Most Optimized Blue: Differences Between UI and User Experience Design with Nick Cawthon
with Nick Cawthon, gauge.io
Brad & Scott talk with Nick Cawthon of gauge. io, who shares highlights from RSA 2026 and his career designing UX for InfoSec/SecOps/DevOps tools.
S2E13
Balancing Innovation and Safety: CTOs Check-In About AI Evolution
Brad & Scott
In this "What's on your mind? " episode of the "How Many CTOs Does It Take?
S2E11
Building Trust with AI: David Espindola on the Path Forward
with David Espindola
I n this episode of "How Many CTOs Does It Take? " podcast, Scott Porad hosts solo and interviews technologist David Espindola about AI.
S2E10
Beyond Transcripts: Language Nuances and Audio Signals with Carter Huffman of Modulate
with Carter Huffman, Modulate AI
Brad & Scott 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 that understands conversations. Carter explains why moderation in gaming is hard because you don't want to ban players unfairly, and contrasts big foundation models with orchestrated ensembles of many tiny models that require high-quality, globally vetted data labeling.
S2E9
Introducing the ADLC: The Agent Development Life Cycle
Brad & Scott
Brad & Scott " 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 a site crash for a Claude wrapper.
S2E7
Predictions and Reflections: One Year Anniversary of the How Many CTOs Does It Take? Podcast
Brad & Scott
Brad & Scott " reflect on the first year of the podcast's publication, discussing Scott's ongoing questions about tech debt and struggles with refactoring, the advances made in AI assissted programming, and the insights they've gained from guests. The episode includes humorous anecdotes about project timeline estimations and dreading conversations about prioritization.
S2E6
Adapt or Fade: Interviewing for Developers in the Age of AI Assisted Coding
Brad & Scott
Brad & Scott explore the evolving landscape of interviewing for programmer positions in the age of AI-assisted coding. They discuss the relevance of traditional leetcode questions, best practices for evaluating skills when interviewees may use AI, and the importance of higher-level thinking in interviews.
S2E5
From Rave Promoter to SaaS Innovator: Revolutionizing Event Management with Ritesh Patel
with Ritesh Patel, Ticket Fairy
Brad & Scott 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 platform tailored for the live events industry.
S2E4
From the Dress Code to the Bottom Line: A CTO Business Primer
Brad & Scott
Brad & Scott discuss the interplay between tech and business. Starting with comments about their own scruffiness and stories of wearing hats to interviews and fancy restaurants, they delve into how CTOs can effectively bridge the gap between technical teams and business stakeholders.
S2E3
The K-Shape of AI Development: Managing Digital Interns
Brad & Scott
Brad & Scott yet again delve into the transformative impact of AI on software engineering. Brad shares his 2025 Cursor Year in Review, revealing his record 2.
S2E2
Setting the Tone: Building Trust Through Security
Brad & Scott
Brad & Scott discuss the role of CTOs in setting a security-minded culture and provide real-life anecdotes of security breaches and incidents. The conversation covers critical frameworks like CIS, SOC 2, and tools like Vanta, Wiz, Drata, and AWS Security Hub.
S2E1
Rediscovering the Joy of Coding through AI with Paul Brown
with Paul Brown
Brad & Scott are joined by Paul Brown to delve into the misplaced fears of AI supplanting engineers, highlighting instead its potential to enhance productivity. Paul shares his journey from skepticism about AI's capabilities to recognizing its strengths, drawing parallels to the historic shift from mainframes to personal computers.
S1E49
Year In Review: How Many CTOs Does It Take To Finish A Season?
Brad & Scott
Brad & Scott announce that they will be taking a two-week break for the holidays and will return with Season 2 on January 13th. They reflect on their first year, discussing the major themes like the challenges of tech debt, the evolving role of AI in software engineering, and the value of weekly conversations with other tech leaders.
S1E48
Turtles All The Way Down: AI Insights with Scott W. Bradley
with Scott W. Bradley
Brad & Scott welcome guest Scott W. Bradley, Managing Partner at Facet Digital, to delve into the complexities and potential pitfalls of AI technology.
S1E47
The AI Race: Who's Ahead, Anthropic or OpenAI?
Brad & Scott
Brad & Scott compare Anthropic and OpenAI's distinct business strategies. While OpenAI takes a high-risk, expansive approach aiming for rapid growth, Anthropic focuses on a more disciplined, business-centric path, particularly targeting corporate customers and avoiding more expensive AI ventures like image and video generation.
S1E46
CTO Therapy: The Risks and Rewards of Vendor Partnerships
Brad & Scott
Brad & Scott delve into Scott's recent meeting with AWS. They discuss the concept of vendors supporting their clients, weighing potential benefits against risks like vendor lock-in and misaligned solutions.
S1E45
Let Them Eat Tokens: AI Efficiency vs. Global Good
Brad & Scott
Brad & Scott 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 explore the current state of AI and its varied impacts, from productivity boosts in small resource-strapped organizations to the political and societal implications of AI adoption.
S1E44
Cabinet Doors Should Open: Avoiding Assumptions in Product Requirements
Brad & Scott
Brad & Scott discuss the critical importance of clear requirements in both hardware and software projects. Using the analogy of a home renovation project, they explore how detailed planning and frequent communication between builders and requesters can prevent costly mistakes and ensure customer satisfaction.
S1E43
The State of AI in 2025: What the DORA Report Reveals
Brad & Scott
Brad & Scott 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 AI, its impact on productivity, and its role in software delivery instability.
S1E42
The AI Hype Cycle: Navigating Growth and Skepticism
Brad & Scott
Brad & Scott reflect on the recent shifts in Big Tech's approach to AI, discussing the changing perceptions and economic impacts of the technology. They provide insights into the AI hype cycle, comparing it to the dot-com bubble, and ponder whether an AI bust is imminent.
S1E41
In Search of the Exceptional: Unpacking the Traits of 10x Engineers
Brad & Scott
Brad & Scott dive deep into the concept of the 10x engineer—those rare developers who are exponentially more productive than their peers. They discuss attributes such as natural talent versus learned skills, curiosity, the ability to think abstractly, and fluidity between high-level design and low-level coding.
S1E40
The Documented SDLC: Why Every Team Needs One (and When)
Brad & Scott
Brad & Scott 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 Life Cycle (SDLC) : what it is, when it matters, and how teams can keep it useful instead of bureaucratic. They explore how the SDLC functions as the connective tissue between engineering, product, and leadership, ensuring teams stay aligned as they grow.
S1E39
Navigating BADD vs. FaDD: Strategic Refactoring in Software Development
Brad & Scott
Brad & Scott dive deep into the engineering crossroads between Better Architecture Driven Development (BADD) and Feature Driven Development (FaDD) . They unpack the eternal question faced by every CTO and engineering leader: Should we refactor now for a better tomorrow, or build features today and clean up as we go?
S1E38
From Specs to Monitoring: A CTO's Guide to QA Best Practices
Brad & Scott
Brad & Scott 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 quality as a chain of practices across the entire SDLC : requirements, technical design, code reviews, unit tests, automation, monitoring, and stakeholder demos.
S1E37
Deploys, Demos, and the Elusive Metric of Engineering Productivity
Brad & Scott
Brad & Scott wrestle with one of the industry's toughest questions: How do you measure engineering productivity? The conversation explores the hypothesis that deploy frequency per person can serve as a practical proxy for velocity, and the cultural tradeoffs this metric may introduce.
S1E36
Product Debt: The Hidden Drag on Innovation
Brad & Scott
Brad & Scott 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 features can quietly slow down innovation, complicate modernization efforts, and create pitfalls when deciding whether to refactor or rewrite.
S1E35
From Streaker Apps to AI Safety Loopholes: What CTOs Need to Know
Brad & Scott
Brad & Scott 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 gets weaker without human content, offering practical takeaways for CTOs.
S1E34
Do Engineering Managers Need to Code? Leveling, Calibration & Craft
Brad & Scott
Brad & Scott delve into the art and science of engineering leveling frameworks. From performance reviews to competency guides, they explore how organizations can fairly evaluate engineers while balancing technical expertise, communication, ownership, and professional judgment.
S1E33
From Prompts to Product: How AI is Changing Software Development
Brad & Scott
Brad & Scott explore 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 a look at recent data showing how the complexity of tasks AI can handle is rapidly increasing—measured by the length of human-equivalent work AI can now complete.
S1E32
From Bugs to Bloat: Product Debt, KPIs, and the Cost of Features
Brad & Scott
Brad & Scott dig into the messy reality of product management effectiveness, and what happens when bugs reveal deeper product debt. They kick things off with a retrospective on a critical login bug that exposed lingering legacy code, sparking a conversation about how product decisions and technical debt intertwine .
S1E31
CTO Therapy: Managing Urgency, Expectations, and Trust
Brad & Scott
Brad & Scott delve into the critical issue of building a sense of urgency and trust within engineering teams. They discuss the importance of schedule accuracy, delivering on time, and establishing dependable processes.
S1E30
From Coldplay to Code: AI Wins, Data Lakes, and the Age-Old Centralized vs. Distributed Debate
Brad & Scott
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 everything from data pipeline migrations to the ongoing debate over centralized versus distributed data teams.
S1E29
Design in the Age of AI: Craft, Tools, and the Future of Creativity
with Vince Dean
Brad & Scott 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.
S1E28
Storytelling, Not Spin: Founder-Led Marketing with Dan Woods
with Dan Woods
Brad & Scott 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.
S1E27
The Outsourcing Playbook Gets an AI Rewrite: Engineering in the Age of AI and Global Teams
Brad & Scott
Brad & Scott 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.
S1E26
From Code to Careers: AI's Disruption of Software and Work Itself
Brad & Scott
Brad & Scott 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.
S1E25
How GenAI Is Changing the Two Guys in a Garage Founder Story
with Justin Wolf & Joe Malek
Brad & Scott 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.
S1E24
Autonomous Engineering Teams: What Works, What Breaks
Brad & Scott
Brad & Scott 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.
S1E23
The End of Programming As We Know It? Justin Kaufman's tips on building fast with AI
with Justin Kaufman, Mount Joy
Brad & Scott 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.
S1E22
From Chicken to Chatbots: Generative AI in Hospitality with Justin Kaufman
with Justin Kaufman, Mount Joy
Brad & Scott 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.
S1E21
Fake Profiles, Real Disruption: What AI Is (and Isn't) Doing to Tech Recruiting with Dave Hardwick
with Dave Hardwick
Brad & Scott 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.
S1E20
Beyond the Resume: How to Hire and Get Hired in Tech with Dave Hardwick
with Dave Hardwick
Brad & Scott 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.
S1E19
Bonus Episode with Greg Conklin: Navigating Hyper-growth and Tech Debt at Groupon and Dropbox
with Greg Conklin
Brad & Scott 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.
S1E18
Culture, Quality, and Tech Debt: Lessons from the Front Lines with Greg Conklin
with Greg Conklin
Brad & Scott 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 .
S1E17
Lessons from the Mountains: Retrospectives and the Secret Sauce of High Performance Teams
Brad & Scott
Brad & Scott 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.
S1E16
Exploring AI, Knowledge, and Ethics with John Helm (Bonus Episode)
with John Helm
Brad & Scott 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.
S1E15
Understanding and Managing Technical Debt: Insights from John Helm
with John Helm
Brad & Scott 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.
S1E14
The Ball of Mud - Tackling Software Monoliths and Decomposing Tech Debt: Strategies and Challenges
Brad & Scott
Brad & Scott 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.
S1E13
Embracing Failure and Innovation: Lessons from Punk Rock with Kevin Goldsmith
with Kevin Goldsmith
Brad & Scott 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'.
S1E12
Navigating Technical Debt and Code Quality in Agile Teams
Brad & Scott
Brad & Scott discuss a recent incident in a small engineering team that highlights challenges of managing technical debt even with skilled developers and robust code review processes. They explore the importance of refactoring in agile methodologies, the pitfalls of large pull requests, and the complexities of quantifying and prioritizing technical debt.
S1E11
The Reality of AI in Software Engineering and the Future of Work
Brad & Scott
Brad & Scott discuss a recent OpenAI study on AI's effectiveness in completing real-world freelance software engineering tasks. They delve into the results showing that AI models completed only 26% of tasks successfully, highlighting current limitations.
S1E10
Tackling Tech Culture and Interviewing: Insights from Ted Neward
with Ted Neward
Brad & Scott welcome special guest Ted Neward, a senior distinguished engineer at Capital One, joins the hosts to discuss the challenges and intricacies of engineering leadership and technology culture. Ted shares his diverse experiences, from his previous roles at Rocket Mortgage and Smartsheet to his current position.
S1E9
The Power of Drafting Implementation Plans: Insights and Strategies
Brad & Scott
Brad & Scott discuss the importance of having an implementation plan in software development. They emphasize the role that written plans play in fostering collaboration and scaling projects.
S1E8
Learning Styles and Team Dynamics: A Journey from Personal Trips to Strategic Decisions
Brad & Scott
Brad & Scott dive into the fascinating world of learning styles and their impact on teamwork in both remote and in-person environments. The conversation begins with Scott's personal trip, transitioning into an insightful discussion about the importance of understanding and leveraging different cognitive styles within engineering teams.
S1E7
Bonus Episode: Challenges and Insights From Using Cursor to Add a Feature to Our Website
Brad & Scott
Brad & Scott discuss their hands-on experience with an AI agent for updating their podcast website. They share the AI's initial success, followed by its struggle with a more complex task, leading to valuable insights.
S1E6
Embracing AI in Software Development: An Interview with Michael Natkin of Glowforge
with Michael Natkin
Brad & Scott welcome special guest Michael Natkin, a distinguished CTO with an Oscar and a James Beard Award. The discussion centers on the transformative impact of AI in coding and engineering, from the use of tools like Cursor and Code Rabbit to the potential of AI agents in automating complex tasks.
S1E5
Org Structures and Measuring Platform Team Success
Brad & Scott
Brad & Scott discuss the critical role of a Chief Technology Officer (CTO) as a bridge between technology and business success. They delve into important topics such as organizing engineering teams, managing tech debt, and the trade-offs between enhancing engineering velocity and reducing operational costs.
S1E4
Effective Staff Meetings: Balancing Structure and Flexibility
Brad & Scott
S1E3
Building Trust and Authentic Connections in Remote Teams
Brad & Scott
S1E2
Embracing Innovation: Introducing the PR FAQ Framework with Marcelo Calbucci
with Marcelo Calbucci
S1E1
Measuring Technical Debt and Technical Investments
Brad & Scott
How Many CTOs Does It Take? Exploring Startups, Process, and Engineering Efficiency In this episode, two CTOs tackle a wide range of topics, starting with the humorous notion of the number of CTOs needed to accomplish common tasks like naming a podcast or establishing coding standards.
Episode 2
Introducing Our Hosts: Scott and Brad
Brad & Scott
Tech Journeys: From Early Internet Days to AI and Beyond In this episode, hosts Scott Porad and Brad Hefta-Gaub share their extensive career journeys in the tech industry, revealing their paths from early consumer-facing internet roles to leading engineering teams at high-growth startups. Scott discusses his rise from building websites at the University of Washington to heading engineering at TaskRabbit, highlighting his ventures in online media, e-commerce, social media, and gig economy businesses.
Episode 1
Introduction to How Many CTOs Does It Take? Podcast
Brad & Scott
How Many CTOs Does It Take? : Bridging the Gap Between Engineering and Business In the inaugural episode of 'How Many CTOs Does It Take?
