In this chapter, the authors present an overview of the role and responsibilities of the system’s administrator. They start with giving a background description on how this activity has been changing within the last decades considering not only the roles but also how the educational background changed and the new challenges regarding high-level IT management. After this contextualization, the authors reproduce some thoughts and experiences shared by experienced IT professionals giving their vision on how the industry has been changing and what would be the future of system administrators. They advance some suggestions and tools that might help IT teams improve their daily work from the technical and organizational point of view and highlight some future points of research concerning educational paths.