Assistant Director of Middle and Upper School

Title of position: Assistant Director of Middle and Upper School

Reports directly to: Director of Middle and Upper School

Department: Administration

Position type: Full-time Exempt, 12 month contract

Location: Antilles School, 7280 Frenchman Bay, St. Thomas, VI 00802

The Assistant Director of Middle and Upper School works closely with the Director of Middle and Upper School to ensure that the mission and vision of Antilles School are fully implemented across grades 6–12, with a primary focus on the Middle School program. The Assistant Director supports the day-to-day operations of the division and provides instructional and cultural leadership to faculty, students, and families.

Key initiatives include supporting the professional growth of teaching faculty, strengthening middle school–specific programming and curriculum, fostering student character development and accountability, and cultivating strong partnerships with parents and guardians. The ideal candidate brings a strong understanding of early adolescent development, instructional leadership skills, and a relational, student-centered approach. Exceptional interpersonal skills, sound judgment, and a calm, steady leadership presence are essential.

• Collaborating with school leadership to advance the goals of the school’s current strategic plan.
• Supporting an environment focused on inclusion and belonging through equitable, restorative, and anti-biased practices.
• Enhancing the Middle School academic and student life program using developmentally appropriate, student-centered best practices.
• Working with faculty committed to reflective practice, collaboration, and continuous professional growth.
• Supporting smooth transitions for students moving from Lower School to Middle School and from Middle School to Upper School, maximizing the benefits of a Toddler–Grade 12 continuum.

• Supports student culture, access, and belonging; designs and oversees Middle School student life initiatives aligned with the school’s mission and values.
• Provides day-to-day instructional and professional support to Middle School faculty, fostering engaging, developmentally appropriate, and reflective learning environments.
• Serves as a primary liaison between the school and Middle School families, building strong partnerships and supporting effective communication.
• Collaborates with the Director of Middle and Upper School to ensure discipline practices reflect a whole-child approach, emphasizing accountability, growth, and restorative practices.
• Works closely with the Student Support Team and families to develop and implement individualized behavioral and academic support plans as needed.
• Collaborates with the Director of Teaching and Learning to plan and facilitate professional learning opportunities, develop resources, and support faculty growth—particularly in middle school pedagogy.
• Oversees coordination of student life programming, assists in planning and leading assemblies and division-wide events, and helps maintain a comprehensive calendar of Middle and Upper School activities.
• Supports admission, re-enrollment, and orientation activities for Middle and Upper School students in collaboration with the Admissions Team.
• Attends Middle and Upper School community events, including advisory activities, athletic events, arts performances, and other student-centered programs.
• Performs other duties as assigned.

• Bachelor’s degree required; advanced degree in educational leadership or a related field preferred.
• Multicultural competence and demonstrated experience working effectively in a diverse school community.
• Deep understanding of early adolescent development and the academic, social, and emotional needs of middle school students.
• Demonstrated success as a strategic thinker and effective leader with a systems-oriented approach to improvement and change.
• Demonstrated knowledge of curriculum design, instructional alignment, and assessment practices at the middle school level.
• Comfort and fluency with educational technology platforms and digital learning tools, with the ability to coach faculty in effective, age-appropriate integration.
• Proven…