Jobs

Position Overview
The Greenwood School seeks an experienced, highly organized, and student-centered Residential Director to lead and oversee our residential life program. Greenwood is a boarding school for students with learning differences, executive function challenges and social emotional barriers. The Residential Director role is central to creating a safe, structured, and supportive residential environment that promotes skill development, independence, and community engagement.

The Residential Director works closely with academic, counselors, and administrative teams to support the whole child and to ensure consistency across residential and academic programs.

About Greenwood

The Greenwood School is a specialized boarding and day school for boys in grades 6 through 12 located in Putney, Vermont. Our mission is to help students with learning differences build the academic, social, and executive functioning skills they need to become confident, capable, and independent learners. Our program emphasizes structure, relationships, accountability, and personal growth within a supportive and collaborative community. At Greenwood, we find what makes each student shine through personalized learning and hands-on, outdoor, and experiential education.

We value professionalism, teamwork, and a shared commitment to helping students develop resilience, self-awareness, and lifelong skills. Greenwood supports staff through thoughtful leadership, strong collaboration, and opportunities for growth and advancement.

Key Responsibilities

• Provide leadership and oversight of the residential life program, ensuring a safe, structured, engaging and supportive boarding environment.
• Supervise, train, mentor, and evaluate residential staff, fostering a collaborative, professional, and student-centered team culture.
• Develop, implement, and monitor residential policies, routines, schedules, and staffing coverage.
• Support students with learning differences through behavioral management, emotional regulation, executive functioning support, and daily living skills, using a strengths-based and trauma-informed approach.
• Collaborate closely with academic staff, counselors, and families to ensure consistency in expectations and support strategies.
• Respond effectively to behavioral incidents and crises, prioritizing student safety, clear communication, and accurate documentation.
• Promote positive community norms, accountability, relationship-building, and restorative practices.
• Oversee residential operations, including student routines, evening/weekend programming, transitions, and logistics.
• Maintain clear, timely, and professional communication with families and internal teams.

On-Call Expectations

• Participate in an on-call rotation, including evenings, nights, and weekends, as assigned.
• Be available to respond to residential emergencies, student behavioral concerns, and staff support needs during on-call periods.
• Provide leadership and decision-making support during after-hours situations.
• Ensure appropriate follow-up, documentation, and communication after on-call incidents.

Required Skills and Qualifications

• Strong executive functioning skills, including organization, planning, prioritization, time management, and follow-through.
• Demonstrated experience in behavioral management and student support, preferably in a residential, LD, therapeutic, or alternative education setting.
• Excellent people skills, with the ability to build trust, manage conflict, coach staff, and communicate effectively with students, families, and colleagues.
• A consistently positive, growth-oriented mindset, with the ability to remain calm, flexible, and solution-focused under pressure.
• Proven leadership experience, including staff supervision and team development.
• Strong judgment and decision-making skills in fast-paced or emotionally complex environments.
• Bachelor’s degree required; advanced degree in education, psychology, social work, or a related field preferred.

Preferred Experience

• Experience working with adolescents with learning differences, executive functioning challenges, anxiety, or emotional/behavioral regulation needs.
• Background in boarding schools, residential programs, or therapeutic environments.
• Familiarity with collaborative, multidisciplinary team models.