Stepping into headship requires more than just ambition—it demands the ability to embrace change with confidence, adaptability, and vision. A growing number of Heads of School began their journey in enrollment management, leveraging their deep understanding of school communities, relationship-building, and strategic planning to transition into headship. But what does it really take to make that leap? In this session, hear from a leading search consultant and three new Heads of School who all got their start in enrollment management. Gain insights on their professional journeys, lessons learned, and the six key skill sets that enrollment leaders should develop to prepare for headship in a rapidly evolving educational landscape, including: --Advancement & Fundraising – Understanding philanthropy’s role in institutional growth --Governance & Board Relations – Navigating leadership dynamics with trustees --Academic Leadership – Balancing mission alignment and programmatic vision --School Finance – Interpreting budgets, endowments, and financial sustainability --Enrollment & Strategic Planning – Shaping long-term school viability --Parent & Community Engagement – Managing expectations and fostering trust Leadership is a journey of continuous adaptation. We'll explore what happens after "happily ever after"—the realities of stepping into the Head of School role, the unexpected challenges (and joys), and how embracing change allows leaders to thrive. Whether you're actively considering headship or simply curious about the path, this session will offer valuable insights, practical takeaways, and inspiration for navigating your next leadership transition with confidence.