The book focuses on the relationships between technological and social innovations, and the new opportunities and challenges that the education system is facing. The authors explore the intertwines between the educational scenarios and the contemporary social, economic and cultural contexts by discussing the Contamination Lab (CLab) experience, which set out in Italian universities with the purpose of promoting entrepreneurial and innovation culture. The cross-fertilization of various disciplines and between the academic and entrepreneurial worlds, in particular, is the starting point of the CLab Naples training model. The CLab Naples was promoted by the University of Naples Federico II, taking advantage of the opportunities offered by digital technologies, the development of scientific and applied research, and the creativity of the youth universe. Since the beginning, its mission has been to bring new skills and promote the creation of innovative enterprises or startups, starting from the relevant technological and cultural transformations that today are affecting both the workplace and knowledge. The experience of the CLab Naples stands as a powerful link between research and enterprises, laboratory and territory, education and jobs, creative innovation and the development of new digital technologies.