How Many CTOs12 Jun 2025

Bonus Episode with Greg Conklin: Navigating Hyper-growth and Tech Debt at Groupon and Dropbox

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 technical debt, team building approaches, and the differing priorities at Groupon's distributed startup-like model versus Dropbox's cohesive, security-focused architecture. The episode also touches upon the role of senior engineering leadership in managing technical debt and optimizing engineering velocity across diverse teams.

00:00 Introduction: The Journey of Tech Debt
00:22 Exploring Hypergrowth at Dropbox and Groupon
01:25 Building Teams and Strategies
03:24 Cultural Differences and Technical Challenges
04:36 Platform and Ops Teams at Groupon vs Dropbox
07:41 Managing Technical Debt and Engineering Leadership
10:23 Conclusion and Farewell

Resources:

How Many CTOs Pod: https://howmanyctospod.com
Scott Porad: https://www.linkedin.com/in/scottporad/
Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/
Greg Conklin: https://www.linkedin.com/in/gregoryconklin/
Greg's Blog: https://gregconklin.com/

#TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #EngineeringProductivity #TeamVelocity #DevCulture #TeamCulture #EngineeringCulture #Agile #TechDebt #OperationalExcellence #EngineeringCultureMatters #EmpoweredTeams #DevProcess #StartupLeadership #EngineeringMaturity #ScalingEngineering #EngineeringOrgDesign #HyperGrowth #HyperGrowthEngineering #ScalingTech #PlatformEngineering #TechnicalStrategy #TechScalability #DistributedTeams #RapidGrowth #TechOrgDesign #GlobalEngineering #TechOps #AcquisitionStrategy #MultiTenantArchitecture #VelocityVsQuality #TechTradeoffs #EngineeringVelocity #SystemDesign #APILayer #InfrastructureStrategy #SaaSScaling

Denne episoden er hentet fra en åpen RSS-feed og er ikke publisert av Podme. Den kan derfor inneholde annonser.

Episoder(94)

What Broke in Tech: Code Quality, AI Guardrails, and the Evolving Software Engineer

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub continue to recap Gergely Orosz's "State of the Tech Industry" talk and focus on what "broke" and "what'...

3 Nov 36min

The State of Tech in 2026: What Changed And What Didn't

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss a Pragmatic Engineer talk on the state of the tech industry in 2026, focusing on what changed an...

27 Okt 32min

The Human Needs in Augmented Coding: A Conversation with Kent Beck

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub interview software pioneer Kent Beck about his background (JUnit, test-driven development, extreme progr...

20 Okt 1h 9min

Preparing for the Worst: Tabletop Exercises, Unit Tests, and Everything In Between

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss TaskRabbit's overnight AWS region migration from us-west-1 to us-west-2, describing the months o...

13 Okt 44min

Understanding The Fear: Adaptive Leadership in the AI Age

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss growing fear about AI among engineers and managers, framing it as an "adaptive moment" requiring...

6 Okt 34min

Simplifying Tech Through Empathy and Understanding with Frank Bravo

In this episode of "How Many CTOs Does It Take?" podcast, host Brad Hefta-Gaub is joined by guest Frank Bravo, a Bay Area technologist who spent 30 years as CTO in local media, helping put a newspaper...

29 Sep 50min

Managing Skepticism: Balancing Tradition and Technology with AI

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss how AI is changing software engineering referencing Kent Beck's idea that AI makes much existing...

22 Sep 49min

From Academia to Industry: Scott Hanson on the Future of AI and Edge Computing

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub interview Scott Hanson, founder and CTO of Ambiq, a company focused on ultra-low-power chips for "intell...

15 Sep 45min