The aim of the Winter School, open to anyone interested in understanding the needs and the possible applications of AI, is to provide a preliminary knowledge about its use in healthcare, to support the training of people able to advance the deployment of AI throughout the economy. While extant programs mainly focused either on AI or on healthcare, the Winter School is intended to jointly provide knowledge in these two highly developing fields. More and more new competencies are required for professionals and all the related stakeholders since modern healthcare and clinical data science is an interdisciplinary field, encompassing statistics, mathematical optimization, classical and deep machine learning, and data visualization. Also, ethical AI strategies should be pursued to foster literacy and legitimacy around AI, especially in the medical field. But training is difficult. At this purpose, this Winter School would allow participants to learn the opportunities deriving from the applications of AI in healthcare and to analyze opportunities and risks associated with the use of AI in healthcare. Moreover, participants will also deepen their knowledge on the ethical implications of the use of AI and other digital technologies, encompassing the individual and social consequences, fostering decision making. Consequently, it is expected to stimulate participants’ capabilities in making judgments in real life and a new management mindset, eventually promoting skill advancement and careers.