Principals are an influential factor in a child’s academic success (Manna, 2015; Louis et al., 2010; Waters et al., 2003). Although the path of influence is often indirect, principals affect student learning by developing and sustaining strong professional learning cultures (Hattie, 2009; Leithwood & Jantzi, 2012). As a result of the complexities surrounding principalship, a desire to understand the attributes, skills, and leadership actions of successful principals persists as an international focus of educational research. This study examines principalship through the experiences of various stakeholders within a school system utilizing a descriptive single case study ethnographic qualitative approach. This approach explores the relationships, experiences, and perceptions between a principal and those vertically aligned to the principal within the system from the teacher level to the superintendent. This study reflects a conceptual framework representing vertical professional learning within a system and several crosscutting cultural constructs supporting conditions for learning and communication across the system. Research methods included a participant inventory, document review, and non-structured interviews with various stakeholders in a single school district. This research supports that creating a learning culture requires a foundation of leadership talent that balances and reflects both instructional and transformative leadership attributes. When those leadership talents are maximized to foster conditions for collective capacity, collective efficacy, and reciprocal accountability, the leader has built a school that relies on its most valuable resource, its people.