The COVID-19 pandemic has further highlighted the importance of the digital transformation of educational organizations. The effects of this transformation process are not limited to the classroom level but extend into various areas of the school, such as Equipment and Technology, Strategy and Leadership, Organization, Employees, and Culture. Against this background, we assessed the status quo of the digital transformation in Swiss vocational schools from the perspective of both school management members and teachers. For this endeavor, two surveys were conducted: the first one in the period from November 2019 to January 2020 (school management members) and the second one between June and September 2020 (teachers). In total, 202 school management members and 1,739 teachers from 62 schools participated in the study. The results of the analyses indicate that the digitization-related dimensions of Strategy and Leadership, as well as Pedagogical IT Support, were perceived better by school management members, whereas teachers considered the areas of Digital Competencies, Attitudes, and Culture to be more advanced. Furthermore, linear regression models show that the dimensions considered important when assessing the status quo of digital transformation differ between the groups. The results emphasize the importance of communication between and the inclusion of all school stakeholders for the successful management of the digital transformation.