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 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 .