The Harley School – Rochester, NY

The Harley School seeks a dynamic, thoughtful, and deeply relational educator to serve as its next Head of Middle School. Serving students in grades 5–8, the Head of Middle School plays a critical role in shaping the academic, social, and emotional experience of early adolescence at Harley.

This is a hands-on leadership role for an individual who knows and loves middle school students, values faculty expertise, and understands the power of presence, trust, and consistency in a small, mission-driven school community.

Position Overview

The Head of Middle School reports to the Head of School and is responsible for the overall leadership, culture, and daily operation of the Middle School division. The successful candidate will be a visible leader who builds strong relationships with students, faculty, and families while stewarding an academically rigorous, developmentally responsive, and joyful Middle School experience. 

Core Responsibilities

Student Life, Culture, and Wellbeing

• Foster a Middle School culture rooted in kindness, fairness, belonging, and respect
• Be a highly visible presence in classrooms, hallways, lunch, recess, and school events
• Know students well and build authentic relationships with each child
• Lead student discipline with consistency, transparency, and restorative practices
• Employ a culturally responsive approach to all student work
• Communicate student issues clearly and consistently with faculty and families
• Support advisory and social-emotional learning programs
• Ensure student safety, voice, and inclusion are central to decision-making
• Protect and celebrate Middle School traditions and joyful community moments

Academic Leadership

• Provide thoughtful instructional leadership aligned with Harley’s mission
• Establish and hone strong academic systems that support staff and faculty in keeping the middle school running smoothly
• Support curriculum coherence, rigor, and articulation across grades 5–8
• Collaborate with Lower and Upper School leaders to strengthen transitions
• Promote strong study skills, executive functioning, and preparation for Upper School
• Partner with faculty on assessment, feedback, and continuous improvement

Faculty Leadership and Support

• Build a cohesive, supportive, and professional faculty culture
• Offer a balance of new and innovative ideas with respect for tradition and experience among staff
• Observe teaching and provide constructive, growth-oriented feedback
• Incorporate an anti-bias lens to professional work
• Encourage collaboration, reflection, and shared practice among teachers
• Advocate for faculty and support them in navigating student and parent concerns
• Communicate clearly, consistently, and respectfully with staff

Family Partnership and Communication

• Communicate proactively and transparently with families
• Build trust through consistency, follow-through, and accessibility
• Engage families through newsletters, meetings, and opportunities for dialogue
• Partner with families while centering student wellbeing and faculty professionalism
• Solicit feedback from families and work towards partnership during challenges

Community Leadership

• Articulate a compelling vision for the Middle School
• Serve as a positive ambassador for the division within the broader school community
• Support enrollment, retention, and the Middle School’s reputation
• Collaborate closely with the Head of School and leadership team

Qualifications and Attributes

• Commitment to diversity, equity, inclusion, and belonging
• Deep understanding of early adolescent development
• Strong relational skills and emotional intelligence
• Experience teaching and/or leading in a middle school setting
• Prior division leadership experience strongly preferred
• Experience with independent schools preferred but not required
• Leadership experience in other mission-centered schools and organizations also considered
• Masters degree in relevant field preferred but not required
• Excellent communication and organizational skills
• A calm, steady, and reflective leadership presence
• Strong knowledge of best instructional practices

What Success Looks Like

• Students feel known, safe, heard, and proud of their Middle School
• Faculty feel supported, respected, and optimistic
• Families trust the leadership and understand decisions
• The Middle School feels joyful, coherent, and stable
• The division is seen as a strength of the Harley experience

Why Work at Harley?

Founded in 1917, The Harley School is known for its progressive approach to education, deep sense of community, and commitment to developing learners who lead lives of purpose. Our rigorous academic programs and exceptional arts curricula are coupled with unique offerings in the Commons, representing our commitment to education for a sustainable future. Harley is recognized as an educational thought leader. At Harley, you'll join a team of passionate educators and administrators who are deeply committed to student-centered learning and innovation, with opportunities for ongoing professional development and growth.

To Apply

In the interest of promoting a diverse and inclusive workforce, The Harley School welcomes candidates from all backgrounds and identities. Our School’s mission statement begins, “We are a diverse, inclusive community of learners.” Along with a cover letter, resume, and list of references, we ask that you provide a personal statement on how you see yourself promoting diversity and inclusivity if you join the Harley community.

The annual base salary range for this position is $100,000 - $115,000 plus a robust benefits package that may include partial tuition remission.The Harley School considers factors such as (but not limited to) the scope and responsibilities of the position, the candidate’s work experience, education/training, essential skills, internal peer equity, and market and organizational considerations when extending an offer.

Start Date: July 1, 2026

Please submit a cover letter, resume, diversity statement, and three references to jobs@harleyschool.org.

Applications will be reviewed on a rolling basis until the position is filled.

About The Harley School

At The Harley School, we foster a thriving environment in which we all become our truest and best selves. Our values, both in school and beyond, are: community, academic excellence, joy in learning, wellness, and sustainability. We believe children are innately curious about the world and joyfully engaged in it. Our faculty cultivate an environment of academic exploration, where taking risks, making mistakes, and engaging in constructive discourse are integral to intellectual growth. Sustainability is an essential element of the framework that drives curriculum and community decision-making in ways that allow us to care for the planet and each other. We encourage compassionate connection within a diverse community, where each individual is valued and supported to reach their full potential. Harley’s breadth of educational opportunities provides an environment for innovation, creativity, and scholarly pursuits that set the stage for student contributions to the greater good while, as our motto states, they “Become What Thou Art.”

Connections working at The Harley School