How Many CTOs12 Juni 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/

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