Authentic student-run enterprises require more than participation — they require structure. This session explores how to intentionally design leadership systems within school-based enterprises that move students from workers to managers. Participants will learn how to create defined leadership roles, develop training and succession systems, build accountability structures, and cultivate student ownership within real business operations.Using a rural high school enterprise model as a case study, this session provides practical frameworks for empowering students with authentic responsibility while maintaining program sustainability. Attendees will leave with adaptable tools to strengthen leadership development in any CTE pathway.