In this session, a Head of School in their first headship—who previously served as a Director of Enrollment Management—and a Director of Enrollment Management in their first year at a new institution offer a rare dual perspective on what actually makes this partnership succeed. Together, they will unpack not only the most common breakdowns in Head–Enrollment relationships, but also what it takes to intentionally build alignment, trust, and shared leadership from the outset. Strong Head–Enrollment partnerships don’t just improve internal alignment—they fundamentally shape how enrollment strategy is understood, valued, and acted upon at the board level. Importantly, this session extends beyond the leadership dyad to explore how strong partnerships enable enrollment leaders to “manage up” effectively, working in concert with the Head to engage boards and finance committees, communicate enrollment strategy, and align institutional priorities with market realities. Participants will leave with concrete frameworks for communication, decision-making, and role clarity; a clearer understanding of how leadership perspective shifts when moving from enrollment to the headship; and practical strategies to strengthen alignment within leadership teams and with boards and finance committees. Participants will also be able to identify common points of misalignment, evaluate and strengthen their own partnerships, and apply strategies for building trust and effectiveness during leadership transitions.