The COVID-19 pandemic forced school leaders to rapidly adopt digital technologies, sparking new awareness and discussions about digital education and its transformation. Despite significant advances, these changes may be minor compared to the potential impact of artificial intelligence and immersive technologies in education. This paper explores digital learning leadership in Ireland’s secondary school sector using the ISTE Standards for Educational Leaders as a guiding conceptual framework. Qualitative interviews with school principals from various secondary school types provide insights into their existing leadership practices and anticipate their future needs. Key findings revealed digital learning visions integrally woven into the school’s broader learning and educational vision and fresh assessments of student digital competence. They highlighted the salience of the school context in decision-making and the drive for more strategic deployment of formal leadership positions and relationships within and between schools. The implication of these findings underscores the imperative of professional learning models for school leaders that are sensitive to the unique context of each school, their bespoke opportunities and challenges, and the rapid advancements in digital technologies.