Tech debt is a serious issue with regard to the health of an organization's software development lifecycle. The longer one holds out on paying off debt, the more expensive the cost is - eventually. In this talk I will recap the strategies Sauce Labs has applied, and the lessons we have learned along the way, to successfully move beyond our legacy web stack. I will also show how we achieved this with zero downtime and a large number of innovative technologies built on top of the battle-proven Django framework.