Head of Upper School

Head of Upper School 2.3 2.3 out of 5 stars 500 W Willow Grove Ave, Philadelphia, PA 19118 Full-time Springside Chestnut Hill Academy 3 reviews Full-time Position Summary The Upper School Head serves as the educational and cultural leader of the Upper School at Springside Chestnut Hill Academy, guiding a vibrant community of students, faculty, and families in grades 9-12. Reporting directly to the Head of School and serving as a member of the Senior Leadership Team, the Upper School Head champions academic excellence, student belonging, faculty growth, and mission-centered innovation. The Upper School Head is responsible for shaping a distinctly SCH experience - one that combines intellectual rigor, creativity, character, curiosity, leadership, and joy. The role requires an experienced educational leader who understands adolescents deeply and who can cultivate a culture where students are challenged academically, known personally, and inspired to think independently and live courageously. Located in Philadelphia and uniquely connected to the Wissahickon Valley, SCH embraces the educational possibilities of both city and natural environments. Our campus - with buildings constructed across three different centuries - reflects both the history and continued evolution of the school itself. The Upper School experience intentionally extends beyond the classroom through experiential learning, leadership development, outdoor education, entrepreneurship, athletics, arts, and innovation. Beginning with the transformative ninth-grade Outward Bound experience, students are challenged to build resilience, independence, empathy, and community throughout their Upper School journey. SCH's Upper School community reflects the breadth and diversity of the greater Philadelphia region, drawing students from more than 90 zip codes across Southeastern Pennsylvania and neighboring communities. Through a significant commitment to financial aid and accessibility, SCH brings together students with varied backgrounds, experiences, perspectives, and aspirations. The Upper School also includes an intentional international student community that enriches the educational experience through global perspectives and cultural exchange. The spirit of SCH is perhaps best captured by the phrase carved into the Alexander Stirling Calder fireplace in the Henry Library in 1906: Kindle Your Own Fire. The Upper School Head helps ensure that students are inspired not only to achieve, but also to discover purpose, cultivate curiosity, and develop the confidence to lead meaningful lives. At SCH, the Upper School experience is defined not only by exceptional academics, but also by authentic opportunities for leadership, entrepreneurship, athletics, artistic expression, robotics and innovation, community engagement, global learning, and real-world experience. The Upper School Head ensures these defining experiences are integrated into a cohesive and mission-aligned student journey.

Primary Responsibilities:

Educational Leadership:

Provide strategic and day-to-day leadership for all aspects of the Upper School program Promote a culture of intellectual curiosity, academic challenge, creativity, and student engagement Lead ongoing innovation in curriculum, teaching, learning, and student experience Support a balanced and student-centered academic environment that values both excellence and wellness Ensure alignment between SCH's mission and Upper School programming

Student ExperienceCulture:

Foster a joyful, inclusive, and relationship-centered Upper School culture where students from varied backgrounds and experiences feel known, valued, and connected Ensure students are supported, challenged, and celebrated throughout their Upper School journey Promote student leadership, character development, ethical decision-making, and belonging Support student wellness and healthy adolescent development Cultivate a community that values empathy, collaboration, curiosity, and mutual respect Partner with students to sustain an engaged, vibrant, and mission-centered school culture

Faculty LeadershipDevelopment:

Recruit, support, evaluate, and retain exceptional faculty and staff Foster a collaborative culture of professional growth and innovation Encourage interdisciplinary learning and mission-driven teaching practices Support faculty leadership development and instructional excellence

Signature SCH Programming:

Champion the distinctive programs and experiences that define the SCH Upper School journey, including: Inter-A athletics and student-athlete development The Center for Entrepreneurial Leadership (CEL) Robotics, engineering, and innovation initiatives Visual and performing arts AP and advanced academic offerings Experiential and community-based learning Outdoor leadership and the ninth-grade Outward Bound partnership Philadelphia-based civic and cultural engagement opportunities Global education and international student experiences Support opportunities for students to engage in meaningful global learning, including international partnerships, cultural exchange, and educational travel experiences Ensure these experiences are integrated into a coherent vision of adolescent education that develops intellectual curiosity, resilience, leadership, creativity, collaboration, and purpose

Community Leadership:

Build strong partnerships with families, students, faculty, alumni, and school leadership Communicate clearly, thoughtfully, and consistently with all constituents Serve as an ambassador for the Upper School and the broader mission of SCH Partner effectively with families from a wide range of backgrounds and experiences Participate actively in admissions, enrollment, and community events

OperationalStrategic Partnership:

Partner closely with the COO and institutional leaders to support the daily student experience Lead Upper School planning, scheduling, staffing, and program implementation Support school-wide strategic initiatives and institutional priorities Contribute to long-range planning and innovation efforts

Desired Qualifications:

Demonstrated success in educational leadership and adolescent-centered learning environments Deep understanding of Upper School students and adolescent development Exceptional communication, relationship-building, and leadership skills Strong commitment to academic excellence and student belonging Experience supporting innovative programming and interdisciplinary learning Ability to lead with empathy, clarity, optimism, and integrity Commitment to diversity, equity, inclusion, accessibility, and community engagement Appreciation for the value of geographic, socioeconomic, and cultural diversity within a school community

Preferred Experience:

Independent school leadership experience preferred Experience leading faculty teams and complex school communities Familiarity with advanced academic programming, athletics, arts, innovation, experiential education, and global learning Experience supporting strategic initiatives and institutional change Experience working with diverse student populations, including international students and families

Leadership Characteristics:

The ideal candidate will demonstrate: Intellectual curiosity Authenticity and humility Joy in working with adolescents Visible and relational leadership Creativity and adaptability Excellent judgment Optimism and warmth Cultural competence and global perspective A deep belief in the transformative power of schools and community

Application Procedures:

Application deadline: September 15, 2026. To be considered, candidates must upload a cover letter, resume, and information for three references through our online platform.