Schools serve as unique environments for fostering the well-being of young people. However, the sustainable implementation of positive education remains a complex challenge. Rather than relying on fragmented efforts, schools should cultivate a coherent and holistic culture of well-being that integrates both explicit and implicit approaches. This chapter underscores the pivotal role of strategic leadership in building a sustainable culture of well-being. Drawing on a systematic literature review, we present a framework of eight strategic pillars that offers an evidence-based foundation for implementing positive education in a consistent and effective manner. Based on interviews with 11 Finnish school principals, we illustrate how these pillars are enacted in practice. We propose that strategic and positive leadership are interdependent and mutually reinforcing. Strategic leadership provides the vision, alignment, and continuity required for systemic change, while positive leadership creates the relational and psychological conditions in which well-being can genuinely flourish.