Rebooting Culture
summary
Runs a postmortem on a three‑year culture rebuild at Rent the Runway where an engineering org of ~15–20 devs hits a cultural segfault and recovers while later scaling to 60 engineers. Details: a monolith → microservices rewrite, removal of brittle git submodules, added automation and feature flags so storefront releases move from weekly four‑hour pain to daily deploys; published career ladders after iteration; introduced blameless learning reviews and concrete practices for psychological safety and healthier meetings.
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chapters (12)
- 0:00Introduction
- 1:01Moving to management
- 4:56The cultural segfault
- 5:55Wake-up call
- 7:31Improving team velocity
- 12:17Building better structure
- 15:58Engineering career ladders
- 18:22Learning from failures
- 20:28Psychological safety
- 24:20Vulnerability and connection
- 27:24Healthy conflict and meetings
- 31:42Key takeaways and conclusion
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