Nuanced understanding of the curricular and co-curricular dimensions of a complex Upper School and particular alignment with Winsor’s commitment to educating young women; Deep knowledge of current and evolving best practices and innovation in Upper School curriculum, pedagogy, and student life; Strong evidence of a personal and professional commitment to diversity, equity, inclusion, and belonging and a track record of shared ownership in nurturing a diverse and inclusive school community; Proven ability to lead thoughtful change while building faculty trust and community buy-in; Administrative experience supporting, supervising, and developing faculty with clarity, consistency, and care; A record of building systems that improve communication, alignment, decision-making, and follow-through; Demonstrated ability to navigate difficult conversations, engage in candid dialogue, and make thoughtful decisions in complex situations; Experience recruiting, developing, and retaining diverse, mission-aligned faculty; and The skill and willingness to teach one Upper School class each year. Relational, approachable, and genuinely invested in the lives of students and colleagues; Energetic and collaborative, building trust, shared ownership, and collective momentum; Calm, flexible, and responsive, with the capacity to troubleshoot effectively in real time and the organizational fluency to manage multiple streams of information and respond to situations as they emerge; Creative and resourceful, approaching challenges with intention, humility, curiosity, and a growth mindset; Strategic and discerning, able to translate ideas into focused, purposeful action; Warm and credible partner to sophisticated, highly engaged parents; Generous-minded community builder who values relationships, traditions, and institutional culture; and a sense of humor, playfulness, energy, and joy in the daily rhythms of the school day.