As organizations are getting more dependent on the use of technologies, it is essential to identify the shape of organization’s digital leaders in order to adapt rapidly into the opportunities of digital transformation and remain competitive. However, there might be gap for leaders in managing this digital trend. This creates a research opportunity to learn about the requirements of leaders in creating new leadership at this digital age. Extant literatures have provided the drivers or determinants of digital transformation, which are customer knowledge, leadership style and contextual factors of organizations. The CIOs, CDOs, and CMOs are the essential candidates in leading digital of an organization. In this paper, the roles and responsibilities of CIO, CDO, and CMO would be examined and the gap occurred between existing capabilities of leaders and new digital leadership will be analyzed.