Posted: 26-Feb-26
Location: Annapolis, Maryland
Type: Full Time
Preferred Education:
Internal Number: HOUS2026
Overview
St. Anne’s School of Annapolis seeks a creative and joyful visionary with a passion for middle years experiential education, a skill of inspiring extraordinary educators, and excellent organization and communication skills alongside a passion for leading independent schools as the School’s Head of Upper School (grades 5-8).
St. Anne’s School is an independent, co-educational Episcopal day school serving students from two years old through Eighth Grade. Nestled in the vibrant, historic seaport city of Annapolis, Maryland—and just a short drive from both Washington, D.C. and Baltimore—our campus is home to a joyful, inclusive, and forward-thinking learning community.
We are recognized for our leadership in progressive, inquiry-based education that is deeply rooted in a robust social-emotional learning (SEL) framework. Our educators are energetic, reflective, and lifelong learners who embrace collaboration, innovation, and student-centered teaching practices.
St. Anne’s School is known for:
- A dynamic and welcoming school culture
- An intentional approach to whole-child development
- A commitment to equity, belonging, and purpose-driven education
- An agile, future-focused mindset in both pedagogy and community life
Whether in the classroom, in advisory, or beyond the school walls, our faculty are mentors, guides, and champions for every student.
Mission
St. Anne’s School of Annapolis invests in the intellectual and spiritual promise of each student in a community that celebrates diversity and upholds the dignity of every human being.
We challenge students to think critically and creatively, to know themselves as learners, and to govern their lives with confidence, compassion, and integrity.
Program
St. Anne’s School’s academic approach is grounded in the belief that students learn best when they are actively engaged, intellectually challenged, and emotionally supported. The research-backed, project-based, and progressive education prepares students not only for academic success—but for a lifetime of critical thinking, empathy, and purpose. This academic approach is:
Rooted in Research, Designed for Real Life
Curriculum is designed around the latest in educational neuroscience, child development, and learning research. This foundation enables teachers to craft intentional learning experiences that challenge students intellectually while nurturing their natural curiosity.
Project-Based: Learning by Doing
Students at St. Anne’s School don’t just memorize facts—they investigate, create, experiment, and collaborate. Through project-based learning, students explore real-world topics in depth, often integrating multiple disciplines such as science, math, humanities, and the arts.
Progressive and Personalized
At the start of each school year, students take time to reflect on what excites them about learning and to write down their personal hopes and dreams for the year ahead. Students set intentions, articulate goals, and envision the kind of learner and community member they aspire to be. St. Anne’s also employs an innovative assessment tool called MindPrint for Grades 3-8, which helps teachers understand each student’s unique learning profile—including their strengths, needs, and how they process information.
Academically Rigorous with Heart
The academic program is rigorous and developmentally appropriate, designed to stretch students’ abilities while also attending to their well-being. Academic rigor and emotional development are not separate goals—they are interconnected.
Socially and Emotionally Growth-Minded
Emotional intelligence, self-awareness, and empathy are just as important as academic achievement. The integrated social and emotional learning (SEL) framework teachers implement helps students learn how to navigate challenges, build healthy relationships, and develop a strong sense of identity and purpose.
Purpose-Driven
St. Anne’s instills a deep sense of responsibility to others and the world. Through the civic-minded curriculum, students are empowered to become active citizens, ethical leaders, and compassionate changemakers.
NOT Limited to the Classroom
Through thoughtfully designed field experiences, students expand their understanding of the world, apply classroom knowledge in real-life contexts, and cultivate a deeper sense of connection to their communities and environment. Field experiences are not isolated events—they are purposeful extensions of academic and social-emotional learning.
Forward-Thinking
By the time students graduate from St. Anne’s School, they are well-prepared for the rigors of high school and the demands of the future. They leave the school as independent thinkers, effective communicators, ethical leaders, and joyful learners.
The Position
The Head of Upper School is responsible for ensuring the thoughtful implementation of the School’s mission across program levels, with faculty, among students and families, and in the leadership setting. The Head of Upper School must understand and have a firm commitment to the mission of St. Anne’s School as an independent, Episcopal day school serving a diverse student and family population. The Head of Upper School must also understand and enact diversity, equity, and inclusion as foundational to the operation of the school and wellbeing of all constituents.
Primary Responsibilities
Administrative Leadership
Support and ensure success of the school strategic initiatives by participating as a key
educational and institutional leader. Duties and responsibilities include but are not limited to:
- Develop, analyze, evaluate, synthesize and innovate in all areas of program, with teaching faculty, and in support of all non-instructional departments.
- Collaborate with the leadership team, including admissions, advancement, marketing and
communications, CFOO, and Heads of PYC and Lower School to achieve strategic and operational goals of the school. - Meet regularly with the Head of School and Program Team to streamline strategic and operational initiatives and duties pertaining to faculty and in all matters relating to students’ academic and developmental progress.
- Commitment to leadership as a team-based endeavor and the collegial, frank, and civil communication and collaboration that team processes entail
- Outstanding attention to detail and accuracy Excellent communications skills, both oral and written
- Ability to manage, evaluate, and motivate staff
- Ability to work with diverse constituencies fairly, respectfully, consistently, and with integrity
- Ability to work both independently and collaboratively while maintaining high professional
standards and at times confidentiality - Engage in curricular evaluation and implementation and overtly support the School’s chosen curricular materials
Faculty
Ensure that St. Anne’s School of Annapolis attracts, retains, guides, and supports extraordinary
faculty. Encourage and supports faculty in their pursuit of excellence in education while fostering
their individual passions and talents. Duties include but are not limited to the following:
- Serve as a vital communication link between and among Upper School faculty and administration
- Work with the Head of School, Associate Head of School, and Head of PYC/Lower School to hire and retain staff
- Collaborate with, support, and oversee Upper School teacher-leaders to ensure delivery of
educational program consistent with the school mission - Conduct formative and summative observations of lead classroom teachers and other links teachers serving Upper School and provide feedback based on observations; provide targeted coaching and/or resources to teaching staff members, both lead and assistant.
- In collaboration with the Associate Head of School. maintain and revise the evaluation and
professional growth frameworks used at the school. - With Head of PYC/Lower School, establish agenda for school-wide staff meetings; with team leaders, establish agenda for program level meetings
- Work in partnership with the Associate Head of School and the Head of PYC/Lower School to design school-wide and program level professional development initiatives
- Coordinate new teacher training/onboarding and mentorship training for Upper School
Curriculum
Ensure that the St. Anne’s School of Annapolis’s Upper School curriculum and innovative educational program is cohesive, consistent, supportive, and reflective of the school's mission and strategic plan. Duties required to sustain and further the school’s leading- edge curriculum include, but are not limited to:
- Oversee curriculum to ensure that the highest AIMS accreditation standards and national benchmarks are met; oversight includes all aspects of development, consistent implementation, and evaluation for academic programs and assessments, social/emotional curriculum, co-curricular programs and athletics
- Research, investigate, maintain, and share knowledge of current initiatives, best practices, and curriculum models to ensure leading-edge, mission-aligned curriculum is employed at the school
- Support schedule design of a progressive educational program, working in concert with the Head of PYC and Head of Lower School
- Develop duties schedule and programmatic events schedules in collaboration with relevant departments
- Initiate and lead the process for peer and leader review and revision of progress reports, newsletters, and communications
- Develop, support, attend, and advise events that highlight curriculum
- Ensure consistent implementation of “rally points” across Upper School grade levels
Students and Families
Ensure St. Anne’s School’s initiative of providing an innovative program and a welcoming community in Upper School, serving as administrative liaison between faculty and parents in matters relating to students’ academic and developmental progress. Duties and responsibilities also include but are not limited to the following:
- With support from the Associate Head of School, develop, evaluate and refine systems for collecting and reporting information between and among faculty and families
- Serve as a support for students, families, and faculty when concerns arise related to student behavior
- Collaborate with School Psychologist and Learning Specialists to support student needs
- Support parent liaison meetings and participate in Parent Association meetings
- Design, schedule, and/or lead events for Upper School
Some highlights of the Upper School student experience include:
Capstone Research Project
The Capstone Research Project is one of the signature programs that students, faculty, and parents universally rave about.
In Eighth Grade, each student undertakes an interdisciplinary project that includes research, expert interviews, community service, creative expression, and a formal presentation to peers, faculty, families, and community members.
Costa Rica Leadership Program
Seventh Grade students may participate in a collaborative international experience that combines cultural immersion, service learning, environmental awareness, global mindedness, and leadership development.
Strategic Opportunities for the Next Head of Upper School
Elevating Project-Based Learning & Academic Excellence
Deepen the commitment to authentic, high-quality Project-Based Learning by providing teachers with the vibrant professional development they deserve. Elevate academic rigor, ensuring that our students are both intellectually challenged and personally known in our uniquely warm school environment. Be sure that the project-based learning outcomes can be easily explained across constituents and documented clearly through curriculum mapping.
Fostering Growth through Positive Accountability
Establish a reliable and transparent framework for student behavior that offers a predictable, division-wide standard. Embracing the role of a "warm demander," ensure that expectations are applied with unwavering consistency and deep care. By eliminating ambiguity, provide students with the security of clear, stable boundaries.
Nurturing Parent Partnerships & Trust
Cultivate a community of mutual respect and transparency with families. Aim to build a partnership where parents feel heard and supported, while clearly understanding the intentionality behind the program. Guide parent expectations with grace and clarity, ensuring the community remains aligned with the core educational mission.
Empowering & Supporting Our Faculty
Serve as a steadfast champion for our educators, providing the professional support that allows them to teach with confidence. Through regular check-ins and targeted growth opportunities, foster a culture of belonging and stability. Aim to make the school a place where the best teachers want to stay and flourish.
Strategic Community Growth
Thoughtfully grow our Upper School by attracting and retaining families who truly resonate with our mission and values. By collaborating closely with Admissions, ensure that our school culture remains vibrant and cohesive, welcoming families who are excited to contribute to and support the unique spirit of our community.
Guided Secondary School Transitions
Partner with the Director of High School Placement to make the journey to 9th grade a productive and celebratory milestone. Aim to provide students and families with the steady guidance and expert insight they need to navigate this transition with confidence, ensuring every student finds a high school home where they will continue to thrive.
Unification of the Upper School Community and Transition Improvement
Bridge the social and academic separation between new students and returning students. Also examine and improve other key transitions, such as the 4th-to-5th and 8th-to-9th grade steps. Consider implementing a "signature experience" for Grades 5 and 6 to help clarify the division's identity by having developmentally appropriate experiences at each grade level.
Preferred Experiences and Qualifications
Knowledge, Skills and Dispositions
- Natural rapport with students with a “kid champion” mindset
- Knowledge of adolescence
- Demonstrated knowledge of management principles and practices
- Ability to use salient data for planning
- Knowledge and familiarity with Project-Based Learning
- Ability to effectively balance multiple competing priorities while maintaining equanimity
- Experience as a relentless problem-solver who takes initiative and contributes as a results-oriented, analytic, strategic thinker
- Meaningful experience identifying and implementing strategic opportunities that lead to measurable improvements across divisions
- Ability to work both independently and collaboratively while maintaining high professional standards and confidentiality
- Excellent organizational skills; ability to establish and manage multiple priorities
- A strong belief in independent school education, and particularly the mission of St. Anne’s School of Annapolis – a mission that shapes all decisions: financial, operational, legal, educational, and ethical
Qualifying Education & Experience
A bachelor’s degree. A master’s degree or higher is preferred
Relevant leadership and management experience in an independent school setting
How to Apply
Educational Directions is assisting St. Anne School of Annapolis on this search. Interested candidates should send a resume, letter of interest, statement of educational and leadership philosophy, and a list of three (3) professional references to the search consultant, Highley Thompson, at Highley.Thompson@edudx.com. Please do not contact the School directly.
St. Anne's School of Annapolis does not discriminate on the basis of race, color, religion, age, gender, sexual orientation, physical disability, or national origin in admissions, employment or educational policies. We value diversity and embrace the fundamental Episcopal belief in the dignity of each human being. We are committed to helping our school community understand and appreciate human differences and similarities.