Digital transformation in schools involves the use of digital data to inform teachers’ pedagogical decisions. Previous research indicates that a deeper understanding of the factors influencing teacher utilization of learning analytics and a comprehensive school context analysis is required. In this article, we conducted a survey study with N = 2,247 teachers in 112 upper secondary schools in Switzerland to examine teacher characteristics and school-related factors that impact teacher use of digital data for pedagogical purposes. The results show that teacher characteristics including their positive beliefs about technologies, competency with digital data, and availability of data technologies significantly predict their digital data use, with differences identified between subject matter teachers and schools. School-related factors about digitalization, such as formal and informal collaboration between colleagues and support from school principals, indirectly influence teachers’ digital data use, mediated by teacher characteristics. Based on these results, personalized support can be formulated for teacher utilization of learning analytics according to their characteristics and the supportive school environment.