How Many CTOs

In this episode of  "How Many CTOs Does It Take?"  podcast, hosts  Scott Porad  and  Brad Hefta-Gaub 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 found...

In this episode of  "How Many CTOs Does It Take?"  podcast, hosts  Scott Porad  and  Brad Hefta-Gaub 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 responsibilitie...

In this bonus episode of "How Many CTOs Does It Take?"  podcast, hosts  Scott Porad  and  Brad Hefta-Gaub 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 nee...

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...

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 man...

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 ins...

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 tec...

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 c...

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 f...

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...

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 insig...

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 de...

  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 fa...

In this episode of  "How Many CTOs Does It Take?"  podcast, hosts  Scott Porad  and  Brad Hefta-Gaub 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...

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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. The conversation transitions to broader topics including the i...

In this episode of  "How Many CTOs Does It Take?"  podcast, hosts  Scott Porad  and  Brad Hefta-Gaub 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...

In this episode of  "How Many CTOs Does It Take?"  podcast, hosts  Scott Porad  and  Brad Hefta-Gaub 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. Through a candid conversation originally recorded in the summer of 2024, they dive into the nuances of translating busine...

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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 withi...

In this bonus episode of  "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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. Key takeaways include the importance of knowing when to reset the AI, providing clear instru...

In this episode of  "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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. The convers...

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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. They emp...

In this episode of  How Many CTOs Does It Take? , hosts Brad Hefta-Gaub and Scott Porad discuss best practices for running effective staff meetings. They explore different meeting structures, including ad hoc agendas, the 'ball of mud' pattern, and structured rhythms for sprint reviews and operations reviews. The duo emphasizes the importance of having a clear agenda to avoid unproductive meetings...

In this episode of  How Many CTOs Does It Take? , hosts Brad Hefta-Gaub and Scott Porad discuss the importance of building trust within a team, especially when working remotely. They delve into personal anecdotes, effective management strategies like office hours, 5-minute summary videos, and regular one-on-ones. Brad and Scott emphasize the role of authenticity, vulnerability, and positivity in f...

In this episode of How Many CTOs Does It Take? , hosts Brad Hefta-Gaub and Scott Porad sit down with Marcelo Calbucci , a seasoned CTO, startup founder, and author of The PRFAQ Framework: Adapting Amazon's Innovation Process to Work for You . Marcello shares insights on the PR FAQ framework—an innovation decision-making tool used extensively at Amazon—and its applicability to startups, product man...

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. They share insights into their professional lives, discussing the intricate dynamics of hiring family, the nuance...