Posted: 05-Feb-26
Location: Pittsburgh, Pennsylvania
Type: Full Time
Salary Details:
Director of Upper School - Winchester Thurston School
Full time, Exempt
This position reports daily to our campus in the Shadyside Neighborhood of Pittsburgh, PA
Position Summary
WT seeks a visionary, relational, and expert educator to lead its Upper School. This leader will enthusiastically embrace and advance the school's mission, lead and support a dedicated faculty, and joyfully interact with students. The Upper School community will welcome a leader who is contagiously passionate and knowledgeable about progressive education, and who will embrace our commitment to equity, inclusion, and belonging, inspire stakeholders, ensure continued innovation, and articulate well the values of a WT education.
The Position
The Upper School, along with its 30+ faculty members, will embrace a leader who is confident, relational, and inspiring. The Director will support a positive and warm community in the Upper School that is marked by strong colleague and student relationships. Faculty members appreciate the collegial culture and seek a division director who is visible and engaged, who will encourage new initiatives and professional development while also allowing for autonomy and independence. A successful Director will take time to understand and support the WT culture and will be a responsive leader who is adept at collaborating and communicating with colleagues to support work and move initiatives forward.
The Director is responsible for the daily operations of the Upper School, working in conjunction with other Upper School administrators. They will need to demonstrate leadership with an ability to envision, develop, and implement an Upper School program that best serves the needs of the students and employees, and maintains our commitment to progressive education.
Opportunities
WT is seeking an energetic, entrepreneurial leader to lead the Upper School faculty in the pursuit of numerous initiatives while also respecting the wellness of our employees and students. These initiatives include some of the following:
- Interdisciplinary Learning: Building on the strengths of an outstanding faculty, WT continues its commitment to progressive education by introducing more interdisciplinary and community based learning experiences. This effort is supported by expanding our campus to include the Joan Clark Davis Center for Interdisciplinary Learning, which opened during the 2023-2024 academic year.
- Schedule and Calendar Innovation: Through our efforts to Rethink Time & Space, WT is engaged in a process to redesign our daily schedule and annual calendars, including moving from a trimester to semester model.
- Social Emotional Wellness: WT is working to enhance social-emotional, wellness and belonging, and DEI learning opportunities through advisory, seminars, and other special programs.
- Strategic Design: WT is in the process of launching the process to create the next strategic design . The leadership team is an essential part of that process.
- Facilitate Growth: Partner with senior leadership to implement a new faculty growth model that advances teaching, learning, and professional culture.
- AI and Technology in the Classroom: Partner with school leadership and faculty to shape a forward-looking vision for AI, technology, and the future of teaching and learning.
Primary Responsibilities
- Serve as an academic leader of the Upper School by:
- Maintaining an educational program that embraces a progressive approach and aligns with WT's Philosophy of Teaching and Learning
- Providing broad oversight and support of the Upper School program by convening and collaborating with Upper School and school-wide colleagues, including Department Chairs, to create an engaging teaching and learning experience
- Serving as an inspirational visionary who drives academic innovation, curricular revision, and collaborative change toward strategic priorities in partnership with the faculty and Dean of Curricular Connection and Innovation
- Ensuring the support, growth, and development of Upper School faculty through collaboration with the Assistant Head of School for Teaching and Learning in regard to onboarding, mentoring, goal-setting, and professional development
- Develop and maintain a culture that values relationships as a critical component of a school community, deepens the sense of belonging, and supports the wellness of everyone
- Advance WT's diversity, equity, and inclusion commitments by actively leading, supporting, and promoting related initiatives with support from the Upper School DEI Liaisons
- Supervise and collaborate with the Upper School Dean of Students and Upper School Counselor in regard to student life and experience
- Supervise and guide the Director and Associate Director of College Counseling in the maintenance of a four-year college counseling program
- Collaborate with the Director of Upper School Admissions to recruit, admit, and retain Upper School students, and support the work of the Advancement Office in engaging alumni and parents
- Support the Director of Athletics with work related to the Upper School athletics program
- Foster meaningful relationships with parents, caregivers, and families through engagement and regular communication
- Develop and oversee the annual Upper School budget in partnership with the Business Office
- Serve on the Academic Administrator Team and collaborate with other academic administrators, including Lower and Middle School Directors; Dean of Curricular Connection and Innovation; Director of Equity, Inclusion, and Belonging; Director of Support Services; Upper School Counselor Gay J. Neals Chair for City as Our Campus; and Assistant Head of School for Teaching and Learning. Also serves on the Head's Council and collaborates with its members as needed
Learn more here.
Winchester Thurston School is an equal opportunity employer. WT is dedicated to the goal of building a culturally diverse and pluralistic community and strongly encourages applications from people of color, LGBTQ candidates, and women
Leadership Qualities
The successful candidate will demonstrate the following in order to be an effective leader of our Upper School:
- Extensive experience teaching as well as academic program leadership with an advanced degree in education or a related field
- Significant knowledge of and expertise in high school curriculum, instruction, and assessment practices
- Demonstrated commitment to academic excellence, innovation, and student success
- Commitment to inspiring and sustaining a culture of excellence with a leadership style that is collaborative, relational, and motivating
- Relevant experience in leading and supporting diversity, equity, inclusion, and belonging initiatives
- Demonstrated success leading curricular, pedagogical, and programmatic change as a strategic thinker, effective communicator, and pragmatic project manager
- Understanding of the importance of interdisciplinary and community-based learning, including equally valuing the arts, humanities, and STEM-related disciplines
- Ability to analyze and develop systems and processes
- Enthusiasm and experience related to hiring, supervising, evaluating, and supporting a large, talented faculty and other colleagues in a respectful and collegial manner
- An evident focus on wellness and community-building as essential elements of a school
- Demonstrated strong communication skills as a speaker, writer, and listener with the ability to approach difficult conversations with directness and kindness while sharing openly about decision-making processes