Most large-scale web companies have over time evolved their system architecture from a monolithic application over a monolithic database to a set of loosely-coupled microservices connected by asynchronous events. This keynote will discuss when, why, and how to make this transformation. It will discuss the architectural challenges and benefits of services, as well as the similar challenges and benefits to the organization itself. Subtly and powerfully, when everything works best our architecture and our organization both mirror and reinforce one another. The presenter has led several of these transformations, and has the scars to prove it. He will share his experiences of companies going through the transition, like WeWork and Stitch Fix, to companies on the other side, like Google and eBay. You will take away actionable suggestions for how to transform your own architecture and organization.