Technology evolves together with humans. Across industrial revolutions, its role has evolved from that of a simple tool used by humans to that of intelligent decision-maker and teammate. In the post-digital era where ongoing advances in artificial intelligence are widely visible, the question arises regarding the extent to which technology will be “upgraded” into roles previously filled by human supervisors, thereby replacing persons in managerial positions. This text aims to delineate how the organizational role of technology has been transformed across decades and the forms that it currently takes within companies, with an eye to the future. We draw on posthuman managerial literature and known cases of organizations where some forms of supervisory artificial intelligence are already used. The text is conceptual-reflective by nature; it seeks to initiate a discussion on the many challenges that humanity will face in connection with the deployment of empowered posthuman agents in companies.