Measurement of teachers’ digital maturity can be useful in diagnosing technology adoption in education and in supporting teachers’ professional development. However, there is a lack of easily usable tools in the existing literature. By investigating the most effective ways to measure teachers’ digital maturity, our research aims to fill this gap. The focus of this article is on a data-driven approach to the assessment of digital maturity in education. Following a process similar to teaching analytics (data collection, data modeling, data understanding and visualization, and contextual understanding), we draw on diary data collected from 12949 French primary school teachers using a virtual learning environment (VLE) during the 2022–2023 school year. Specifically, the paper presents results related to modeling and visualizing data. To this end, we propose a critical analysis of two automatic classification techniques, one supervised rule-based and the other unsupervised (hierarchical clustering). In addition to providing different scales to measure, we have proposed a new approach to diagnose and visualize digital maturity. In this way, the method provides insight into the diversity and intensity of technology use, contributing to a better understanding of digital maturity and providing a practical tool for assessing day-to-day teaching practices.