CTO and the Board
Communicating technology strategy upward: boards, founders, and non-technical stakeholders.
Episodes
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.
CTO and the Board
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?
CTO and the Board
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.
CTO and the Board
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.
CTO and the Board
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.
CTO and the Board
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.
CTO and the Board
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.
CTO and the Board
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.
CTO and the Board
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.
CTO and the Board
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.
CTO and the Board
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 .
CTO and the Board
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.
CTO and the Board
Articles
How can AI be used for revenue generation rather than just cost reduction?
How can companies effectively manage time zone differences with global engineering teams?
How can engineering leaders effectively manage technical debt in a startup environment?
How can retrospectives improve decision-making in high-stakes environments?
How can systems thinking improve innovation speed in engineering?
How did Groupon and Dropbox handle hyper-growth differently?
How do different Generative AI tools compare in app development?
How does Generative AI impact the speed and cost of developing a niche app?
How does organizational structure impact engineering team performance?
How is AI transforming the tools used by tech recruiters?
What are the key elements to include in a resume for a software engineering role?
What are the key factors for successful autonomous engineering teams?
What challenges do fake profiles pose in tech recruiting?
What mindset shift is necessary for effectively integrating AI into business processes?
What role does company culture play in the success of engineering teams?
What strategies did Groupon use to manage technical debt during its rapid expansion?