With this issue of Cutter IT Journal, we aim to bring more perspective to the question of how to digitally transform. All the contributing authors agree that digital transformation will be profoundly complex, but this complexity does not prevent them from bringing useful perspectives to the table and suggesting approaches for how to frame and launch transformation. This issue does not glorify startups, big-bang disruption, or Silicon Valley; it does, however, investigate what lessons incumbents can take from digital natives. It also broadens the scope to include historical framing of the challenge, as well as the authors' rich experience and expertise in working with incumbent organizations.