Chief Digital Officers (CDOs) are establishing themselves as new executives at the top management level of companies that go through a digital transformation. The full article is based on six case studies of CDOs and describes how they fulfill their positions. Five of the cases are from the “CDO Recommended” region of the figure and one from the “CDO Can be Helpful” region. From these cases, we identify the main factors that drive the employment of CDOs, the three role types that CDOs primarily play and the skills and competencies they should have for each role type. We also present four key lessons that will ensure businesses equip their CDOs with the skills to successfully navigate through their digital transformation journeys.