In Sweden, the digitalization of K-12 schools has been ongoing for more than 30 years. Several larger governmental initiatives targeting issues such as the one-to-one classroom and teachers’ development of digital competence have been carried out, but the outcomes have not been as positive as hoped for. In the research literature, there is growing evidence of the importance of long-term and well-anchored strategies, such as functioning information and communication technology (ICT) plans, as well as calls for a system approach to understanding the leadership needed for the digitalization of K-12 schools. There is also research highlighting the importance of applying multilevel analysis for understanding ICT implementation and educational change. In autumn 2017, the Swedish government suggested one such strategy for the digitalization of Swedish schools. One interesting aspect in the strategy is the aim indicating that students, teachers, and school leaders, as well as other staff members working in the schools, should develop what is called “adequate digital competence.” Departing from data gathered within a 4-year longitudinal Swedish research project investigating the advanced use of information technology (IT) in upper secondary schools, this paper focuses on educational IT strategists/managers that work on a municipality level and their role in the process of developing digital competence in schools. Through semi-structured interviews, three educational IT strategists working in three different Swedish municipalities provided their views about their work description, their functions as strategists/managers, and their understanding of digital competence. The first analysis shows clear variations regarding, for example, how the strategists formulate their own role in the ongoing digitalization of the school, as well as under which conditions they can carry out their work.