Migration of IT infrastructure to the Cloud transforms enterprise data, applications, and services to one or more other Cloud environments. Cloud migration engagements often rely on an in-depth discovery of the client's (source) IT environment, which is rather costly and can take up to six weeks before any meaningful conversations with customers can begin about the migration itself. There is a demand for a more agile approach to enable sales teams to perform rapid qualification of cloud fitness and reason about the benefits of Cloud using minimal information from the clients. The existing, consulting based approach typically relies on a number of discovery and analysis tools, yet the entire process is manual, expensive, and time consuming. In this paper we present a suite of cloud transformation analytics (CTA) services designed to streamline the process of premigration and migration analysis, such as cloud fitness validation and consolidation recommendations. CTA supports reasoning about diverse target clouds, as well as various transformation methods to match clients' needs, such as image migration, workload migration, and cross platform migration. We discuss our key insights and lessons learned from employing cloud fitness validation capability on datasets of up to 2000 servers to enable and accelerate the process of migration.