Learn how Wellington Management, a global investment management firm that manages more than 1 trillion USD on behalf of its clients, is executing an all-in strategy to exit all of its physical data centers by 2019. The migration includes both commercial applications and a large number of custom-developed analytical, portfolio management, and trading applications. We share the lessons learned, both positive and constructive, by a team that has been on this journey for over five years. We also discuss usage of many key AWS services, including Amazon Virtual Private Cloud, AWS Direct Connect, Amazon EC2, Amazon ECS, AWS Lambda, Amazon Redshift, Amazon Relational Database Service, and others.