Reports directly to: Director of Middle and Upper School

Department: Administration

Position type: Full-time Exempt, 12-month position

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

Start Date: July 1, 2026, or sooner if available

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.

Opportunity Highlights:

• 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.

For more information about this role please visit https://www.antilles.vi/about/employment .

• 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 ability to supervise, coach, and support faculty through observation, feedback, and professional growth conversations.
• Strong communication skills, including the ability to build trust with students, families, faculty, and colleagues.
• Commitment to advancing diversity, equity, inclusion, and belonging initiatives and practices.
• Experience or demonstrated knowledge of student support services and resources for students with mild to moderate learning differences.
• Minimum of five years of teaching and/or relevant educational leadership experience.

About Antilles School

Antilles School is an independent coeducational day school located on St. Thomas, in the US Virgin Islands. Antilles enrolls approximately 400 students in a toddler program through grade 12. Excellence, Diversity, and Community are the guiding principles for each day at Antilles. Antilles School is committed to the pursuit of educational excellence and a purposeful life. We foster a sense of community, embrace diversity and creativity, seek to develop the whole child, and prepare students for success in college and beyond.

Connections working at Antilles School