The digital transformation of our society in the last two decades has accelerated the pace of innovation. This current environment, characterized by ubiquitous connectivity and complex social networks, demands novel forms of leadership and management in order to compete, collaborate and create value in the digital economy. This course starts with historical developments of digital cultures, then offers a wide perspective of the digital cultures of our times in order to better understand the challenges faced by organizations, from the personal implications for students and future professionals to the challenges in different areas, such as business, economy, politics, and humanities. We will examine the social impact of technologies (such as big data or 3D printing) discuss strategic issues in the digital society (such as copyright, privacy and security as well as new trends in learning), and experiment with one of the most recent innovation approach, Design Thinking. The course requires an active participation by the students that will be required to develop their own digital reputation (one of the key topics of the course) as the main indicator for their assessment.