Last year, a small team at GitHub set out to migrate a large portion of the application that serves GitHub.com to Kubernetes. This application fits the classic definition of a monolith: a large codebase, developed over many years, containing contributions from hunderds of engineers (many of which have moved on to other things). In this presentation, we'll cover our motivations for this migration, the factors that led us to choose Kubernetes, the strategies we used to empower a small team to make a change that affected a large engineering organization, and reflect on what we learned in the process.