Boca Raton, Florida
Posted: 25-Mar-26
Location: Easton, Maryland
Type: Full Time
Salary: $65,000 to $80,000
Categories:
Salary Details:
Required Education:
The Country School is an independent, coeducational, PK-8 school founded in 1934 with a current enrollment of 325 students. Located on Maryland’s Eastern Shore, a few blocks from downtown historic Easton, we offer a challenging academic program in a nurturing environment focused on educating the whole child.
The Dean of Students is responsible for student culture and conduct and upholding the core values of the school. The ability to support students and parents in approaching disciplinary issues with a growth mindset is essential. Prior professional experience leading difficult conversations and restorative practices will ensure a smooth transition.
The Dean is a member of the administrative team and focuses their work primarily in the Upper School (5th-8th grade). This role collaborates with the Lower School, particularly the transition from 4th to 5th grades. The Dean supports Advisors and Homeroom teachers with community-building activities, tracks and supports student service learning projects, supervises student clubs, participates in Outdoor Education trips, and works with the Division Heads and Grade Captains to manage the calendar of student events.
The TCS Seminar course, offered for each grade level in the division, is coordinated by the Dean and includes strands focused on study skills, health, social-emotional learning, and digital citizenship. The Dean and other faculty teach various strands as needed. Additionally, the Dean may have the opportunity to take a leadership role in developing a new Capstone learning experience that brings together project, purpose, and experiential learning for students in 7th and 8th grades.
Student Culture & Conduct
- Communicate and consistently enforce school-wide behavioral expectations and the student code of conduct.
- Working closely with the Division Head, manage student discipline in a fair, restorative, and developmentally appropriate manner, maintaining accurate records of all disciplinary actions.
- Lead restorative practices and conflict-resolution processes among students and between students and teachers.
- In collaboration with the Division Head, coordinate and oversee detention, in-school suspension, and re-entry meetings following out-of-school suspension.
- Investigate and respond to reports of bullying, harassment, or threats in accordance with school policy and applicable law.
- Partner with the school counselor to serve as a primary point of contact for students experiencing social, emotional, or behavioral challenges.
- Collaborate with school counselor to develop and implement student support plans.
- Facilitate student-led initiatives such as peer mediation, student government, and anti-bullying programs.
Family & Community Partnership
- Communicate proactively and professionally with families regarding student behavior, attendance, and well-being.
- Partner with Advisors and Homeroom teachers on service learning projects and enhance the community spirit of these groups.
- Build trusting relationships with families from diverse backgrounds and serve as a culturally responsive liaison.
Administrative Responsibilities
- Maintain accurate and confidential records of all student disciplinary incidents and related correspondence.
- Assist with scheduling, staff supervision, and special event coordination as needed.
- Cover classes when necessary for teacher absences.
- Participate in grade-level and student support team meetings, professional development, and leadership team meetings.
Education & Experience
- Master’s degree in Education, School Administration, Counseling, or a related field preferred; Bachelor’s degree required.
- Minimum 7 years of classroom teaching or school counseling experience, preferably at the middle school level.
- Prior experience in student discipline, student services, or school administration strongly preferred.
Professional and Personal Qualifications
- Deep understanding of adolescent development and the social-emotional needs of middle school students.
- Strong knowledge of restorative practices and trauma-informed approaches.
- Excellent interpersonal and communication skills with students, staff, and families.
- Ability to de-escalate conflict, remain calm under pressure, and make sound decisions quickly.
- Commitment to equity, inclusion, and culturally responsive practice.
- Proficiency in student information systems (e.g., Veracross, Blackbaud) and Google Workspace.
- Ability to maintain confidentiality and exercise professional discretion.
Qualified applicants should submit a cover letter and resume to:
Emily Beck, Upper School Head
The Country School Diversity Statement
The Country School believes that seeking and valuing diversity of ideas, experiences, and identities, developing meaningful connections, and fostering a sense of belonging are vital to each student’s education and growth. A diverse, inclusive, and equitable school community is critical for preparing students for a role in a complex, pluralistic, and interconnected society. We actively see and value the differences of our school community, among them ability/disability, age, ethnicity, faith traditions, family composition, gender identity and expression, learning styles, race, sexuality, and socio-economic status.
Equal Opportunity Employer
The Country School is an equal opportunity employer that does not discriminate on the basis of race, color, religion, age, sexual orientation, gender, nationality, or ethnic origin.