Oakwood School is a private school in the DC Metro area serving students in grades 1-8 with language-based learning differences. Oakwood provides a highly specialized academic environment where students build both skills and confidence. 

The Dean of Student Life’s primary responsibilities include cultivating a safe, structured, and supportive school environment that reflects Oakwood’s mission and values. This role oversees student behavior, school culture, and student life operations, ensuring consistency in expectations, accountability, and the overall student experience. 

This position works collaboratively with other members of the Academic Team and serves as a partner to the Dean of Academics, strengthening systems, consistency, and alignment across the student experience. 

A strong candidate will combine genuine connection with students, steady judgment in moments of conflict, and the ability to communicate with families who are deeply invested in their child's success, all within a school where behavior is understood through the lens of learning differences.

Key Responsibilities

• Develop, maintain, and enforce school-wide systems and policies for student behavior, expectations, and community culture. Develop and maintain school-wide behavior systems while staying closely connected to students through regular check-ins, advisory support, and visible presence during the academic day. 
• Oversee student discipline and serve as the primary decision maker for escalated behavioral concerns. Lead student discipline through direct, relationship-based intervention focused on increasing individual accountability and growth. 
• Coach and support faculty in effective classroom management and consistent implementation of student life expectations. 
• Oversee student life operations, including internal student-facing events and scheduling of staff duties for lunch, recess, arrival, and dismissal. 
• Serve as liaison to the Oakwood Parents Association (OPA) and support student leadership initiatives. 
• Collaborate with leadership on hiring, onboarding, school planning, and crisis response. 
• Support admissions and communications/marketing efforts through event participation and content review.

Required Qualifications

• Bachelor’s degree in Psychology, Education, Counseling, or related field from an accredited college or university. 
• Minimum of 5-7 years of experience in a school setting with increasing leadership responsibility. 
• Demonstrated experience managing student behavior and supporting faculty in classroom management. 
• Strong understanding of child development and behavior, particularly in students with learning differences. 
• Proven ability to coach and support adults in a professional setting. 
• Excellent communication skills, including experience working with families in complex or sensitive situations. 
• Ability to exercise sound judgment, maintain confidentiality, and manage competing priorities.

Preferred Qualifications

• Master’s Degree in Psychology, Education, School Leadership, Counseling, or related field from an accredited college or university. 
• Experience in a private or independent school setting. 
• Experience working with students with specific learning disabilities. 
• Training in behavior frameworks (e.g., Responsive Classroom, PBIS, restorative practices).
• Background in counseling, social-emotional learning, or student support services.
• Experience leading school-wide initiatives related to student life or culture.

About Oakwood School

Oakwood School is a private 1st-8th grade, co-ed day school for bright students with learning differences. Oakwood School provides a multisensory educational program in which students with learning differences are guided to achieve their unique academic and social potential in a nurturing community environment

Connections working at Oakwood School