Appreciate you laying this out so clearly! I have a few questions: 1) How did you handle scaling? 2) What was your approach to migration? 3) Did you encounter any issues with consistency? We're considering a similar implementation and would love to learn from your experience.

One thing I wish I knew earlier: starting small and iterating is more effective than big-bang transformations. Would have saved us a lot of time.

Additionally, we found that the human side of change management is often harder than the technical implementation.

While this is well-reasoned, I see things differently on the timeline. In our environment, we found that Vault, AWS KMS, and SOPS worked better because automation should augment human decision-making, not replace it entirely. That said, context matters a lot - what works for us might not work for everyone. The key is to focus on outcomes.

One thing I wish I knew earlier: cross-team collaboration is essential for success. Would have saved us a lot of time.

One thing I wish I knew earlier: documentation debt is as dangerous as technical debt. Would have saved us a lot of time.