This is NOT a session about MS DevOps tools. This is the story of how the Azure DevOps team transformed from shipping an on-premise server product every couple of years, to shipping a cloud service multiple times a day. In the process, almost everything about how this team of 800 people work has changed. We had to figure out how to do agile at scale, how to transform into a microservice cloud architecture, completely restructure teams and roles, throw out a suite of 10’s of thousands of tests and start over, and go from zero telemetry, to 8+TB/day, as well as figure out how to interpret the data. Many mistakes were made along the way, and I'll be sharing the good, the bad, and lessons learned.