This document discusses enterprise transformation and moving to the cloud. It notes that 70% of large change programs don't meet their goals. It discusses framing enterprise transformation as an "hourglass" with time against obsolescence. Successful transformations take a holistic approach with top-down and bottom-up sponsorship. The typical elements of a total cost of ownership analysis are discussed, but it is noted that looking only at TCO can disrupt a business case and strategic benefits should also be considered, which are usually 3 times the net TCO value. Savings from transformation should be reinvested in digital innovation.