Adopting new technologies such as Kubernetes is a big change for traditional enterprise environments. Ancestry was a typical Microsoft .NET shop running in a traditional IT environment. During the past year and a half Ancestry has adopted containerization and micro services orchestrated by Kubernetes. This presentation will describe Ancestry's journey to Kubernetes. We will discuss what we have learned during these past few years from a technical and cultural perspective. This presentation will provide insights to help companies make such a transition.