Dean of Students

Position Type: High School Certified Positions

Date Posted: 6/2/2026

Location: The Gilbert School

Date Available: 08/17/2026

The Gilbert School located in Winsted Ct in northwest corner of CT is a comprehensive middle school/high school grades 7-12 quas-public, independent school. The Dean of Students serves as a key member of the school leadership team and is responsible for supporting a positive, safe, and engaging school environment that promotes success, personal growth, and academic achievement. The Dean works collaboratively with the administrators, faculty, staff, students, and families to strengthen school culture, implement behavior expectations, support student engagement, and promote consistent application of school policies and procedures.

The Dean of Students plays a visible role in the daily school operations and serves as an advocate for students while maintaining high expectations for accountability, respect, and community standards.

The Dean of Students is responsible for supporting student discipline, attendance, safety, and school climate while enforcing Board policies and Connecticut state laws.

• Minimum of five years of teaching experience at the middle or high school level
• Connecticut Administrative License (#092) preferred but not required

• Work collaboratively with teachers regarding student behavior and support plans
• Collaborate with the Guidance Department on discipline, student goals, and restorative practices
• Support the Director of Curriculum in addressing classroom management concerns and supervise the PM School program, including staff monitors and procedures
• Help students in grades 7–12 maintain high standards of behavior and conduct
• Assist in developing and maintaining campus safety and security procedures
• Maintain regular communication with parents regarding discipline and school-related concerns
• Report illegal activity to appropriate authorities and maintain documentation
• Ensure compliance with Special Education laws, PPT procedures, and IEP requirements related to discipline
• Facilitate student re-entry meetings following suspensions and provide peer mediation when appropriate
• Maintain accurate disciplinary records in electronic and physical formats
• Meet with parents, teachers, counselors, support staff, and students regarding student discipline and welfare

• Monitor student attendance and enforce school attendance policies
• Conduct attendance hearings with students, families, and school representatives
• Monitor lunch periods and common areas to maintain a safe environment
• Supervise hallways before school, during passing periods, and at dismissal
• Work with the administrative team to improve school climate and student behavior

10-month position with comprehensive benefits

Postings current as of 6/17/2026 9:28:16 PM CST.