Organizations need to digitalize to be competitive in the market. Failure to change means failure to survive. This means that organizations need to understand - at a high level - what needs to change to become successful digital organizations, and then come up with strategies to facilitate those changes. Analytics that help understand the trade-offs between choosing certain paths are critical to decision-making. Further, a clear understanding of the impacts of those strategies on the enterprise architecture will enable creation of roadmaps that can be used to communicate and monitor execution for successful transformation. In this portfolio playbook session, we take a closer look at how EA supports strategy definition, development and road-mapping.