The labor market has always been subject to transformations driven by technological advancement. Among the big innovations that are changing the labor market are robotization and digital work platforms. According to the report prepared by the International Labor Organization (ILO) in February 2021, unprecedented opportunities are being created for workers, businesses and society but, at the same time, serious threats to both the dignity of work and fair competition are emerging. Under the European Union’s magnifying glass are primarily Artificial Intelligence (AI), robots and smart working. The World Economic Forum (WEF) in a recent report stated that “a new generation of intelligent machines could replace a large part of human jobs”. These changes impose a deep reflection on the main challenges, starting from the rethinking of welfare systems; the creation of innovative professionalism and competences with the related new employment framework and, finally, the need to regulate the application of smart working, AI and robotics in companies and in the world of work.