Upper School Principal

Who are we looking for?

The Upper School Principal, in partnership with the Head of School and the School’s Leadership Team, will serve as lead learner, role model, community builder, and relationship curator of Upper School (9-12), comprising grades 9 - 12, with approximately 520 students, and more than 70 faculty. The US Principal is expected to be a proven administrator or department leader with the necessary skills for working with a dynamic faculty, a diverse student population, and a dedicated parent community.

This leader will be expected to lead and inspire a talented team of professionals and to partner with other leaders and stakeholders within the school to ensure that the strategic direction and vision of Upper School is consistent with and reflective of what is happening in the other two levels. The US Principal should also be a team player who has a warm collaborative nature, positive energy, sense of humor, and can be both a consensus builder and decisive decision maker.

This person must understand the importance of accountability and consistency in leading people, managing programs, and creating initiatives. The ability and skill to prioritize and organize the work along with being self-motivated to complete the work is a must given the fast-paced and multi-faceted nature of Upper School.

The Upper School Principal oversees the daily operations of the division, including budgeting, staffing, and the overall cultural health of the community, while cultivating a faculty and staff environment where individuals feel seen, valued, and supported. This leader fosters a student experience grounded in growth, trust, and accountability, balancing inclusion with clear expectations and shared community norms. Working collaboratively across the School, especially with the Lower and Middle School Principals, the US Principal helps advance and uphold the value of a Dwight-Englewood education both internally and externally.

As the chief administrator of the Upper School, the Principal partners closely with faculty, department chairs, the Upper School administrative team, and Student Support Services to ensure alignment, coherence, and excellence in curriculum and programming, setting the tone for the division through high professional standards, integrity, and purpose-driven leadership.

This role might be for you if you are…

• A thought leader with the knowledge and expertise to work with all school constituencies and to do so with warmth, consistency, inclusiveness, and a sense of humor
• A strategic and focused leader who can maintain exceptional attention to detail while staying adaptable in high pressure situations
• A master communicator who can vividly and in multiple ways tell our story and make known the value proposition of a Dwight-Englewood educational experience and who can be a highly visible, approachable, and strategic leader who values the importance of positive, effective, appropriate, and accurate communication
• A community builder who is a highly skilled creative collaborator and has the ability and vision to lead, manage, supervise, support, and advance all matters related to the administration, faculty and staff, operation, budget, policies, procedures, facilities, and structures of the Upper School program with calm and grace
• An educational enthusiast and aficionado who can develop, maintain, and ensure that all policies and guidelines for faculty, staff, and students are in keeping with the mission and educational best practices
• A believer in the beauty that all types of diversity and perspectives bring to a community who can recruit top, diverse candidates for consideration for employment
• A leader with integrity and character who knows how to manage faculty, student, and family expectations in a manner that is honest, caring, and empathetic and can handle sensitive information with confidentiality, discretion, thoughtfulness, and diplomacy
• A highly skilled decision maker who can discern the need for individual action versus broad input
• A lifelong learner committed to continuous improvement and reflection both personally and professionally
• A team player who can work in cooperation with…