Student well-being is important for inclusive societies and academic achievement. As studies have shown, well-being is associated with school success. Today, it's common for schools to use different technologies to collect and analyse digital data with the purpose of improving educational outcomes. Generally, this collected data focus on student engagement, attendance, and results, with novel advancements being aimed at supporting student well-being. In this pilot study, we analyse teachers' experiences to identify benefits and challenges during a spearhead integration of a data-driven tool for examining student well-being in upper secondary school. Using thematic analysis of teacher interview transcripts, we identified four themes: insight diversity, caring pedagogies, teacher leadership tools, and faculty transformation. The themes are discussed using the theoretical perspectives of orchestration, practice, process, and actors. Key results show that some high-value benefits teachers report on are gaining insights, saving time, and informing decision-making. The challenges include a lack of systematisation, guidance, and resources, and tensions related to defining the role and responsibilities of a teacher or mentor. We conclude that schools that work to support student well-being can benefit from the diversity of insights and practices related to the presented tool. However, an informed and systematic approach would be needed to leverage the benefit of spearhead integration. The contribution of the study is to provide insights on how a well-being tool can be used in an educational context to bring understanding of student well-being to teachers. Our results may inform decisions and guide integration and implementation practices in schools.