Westwood High School seeks a student-centered and forward-thinking educational leader to serve as Dean of Students beginning in the 2026–2027 school year. In partnership with the Principal and Assistant Principal, the Dean supports student learning and helps lead the development and implementation of systems that promote belonging, engagement, and student success. The Dean works closely with students, educators, families, and community members to strengthen instructional practice, cultivate a positive school culture, and develop systems that support students and respond to the evolving needs of the school community.

This is a school-year position that includes limited summer work days (including August 2026).

 

Our District:

Westwood is a welcoming suburban community with an exceptional track record of supporting and celebrating its public schools.  As a district, we are committed to creating an environment where diverse perspectives and backgrounds are embraced, and we understand that a diverse team allows us to serve our community better. We welcome and encourage individuals of every race, color, ancestry, national origin, religion, age, gender, marital/domestic partner status, sexual orientation, gender identity, disability status, and veteran status to seek opportunities within our school district.

 

You will join the strong professional learning community of the Westwood Public Schools. In our mission to prepare students for college, career, and civic life, we work collaboratively to provide rich and rigorous curriculum, high-quality instruction, trusting relationships, and authentic educational experiences.  We hold true to our core district values of academic excellence and a commitment to improvement; curiosity and tenacity; and respectful relationships in a caring, collaborative community. 

 

Our School:

Westwood High School is a thriving community of hardworking and thoughtful students, families, and staff. With approximately 900 students from grade 9 through age 22, the school maintains a small-school feel while offering a comprehensive array of academic programs, co-curricular activities, and support services.  Our educators model and encourage a deep investment in learning.  Coursework focuses on preparing students for college and careers while also providing them with opportunities to try new things and explore their passions in depth.  WHS is a proud METCO school, with strong program leadership and an unwavering commitment to supporting the values of the nation's oldest and most successful public school racial integration program.  

 

Qualifications: 

• Massachusetts educator license required; Massachusetts certification (or eligibility for certification) as a Supervisor/Director or Principal/Assistant Principal required
• Master’s degree in education or a closely related field preferred
• SEI endorsement required
• Five years of experience in K-12 education required; some leadership experience within a high school or community program preferred
• Experience and demonstrated skill managing long-term projects and initiatives
• Ability to skillfully and thoughtfully handle a multitude of varying and complex issues with creativity and empathy
• Demonstrated commitment to celebrating diversity, pursuing equity, and promoting integration
• Familiarity with trauma-sensitive educational practices

 

Responsibilities:

 

Student Support and Success

• Communicate and uphold high expectations for student behavior and achievement in alignment with the Westwood Portrait of a Graduate
• Promote student investment and belonging in academics, co-curricular programs, and the broader social and civic life of the school community
• Co-chair the school’s Child Study Team, coordinating collaborative problem-solving processes that address student needs within the school’s Multi-Tiered System of Supports (MTSS) framework
• Identify and analyze academic, behavioral, and attendance data to address barriers to learning, inform student-centered decision-making, and guide schoolwide support efforts
• Partner with educators, counselors, and families to develop team-based approaches to student support that promote student growth and well-being
  

Instructional Leadership

• Coach educators in the development of growth plans that foster student and educator learning
• Conduct regular classroom visits and engage educators in reflective conversations that center effective teaching and student engagement
• Support educators in implementing inclusive, culturally responsive, and developmentally appropriate instructional practices that provide multiple pathways for engagement and student learning
• Contribute to the design and facilitation of professional learning that supports students’ academic, social, and emotional development and fosters a culture of reflection and continuous improvement

Operations

• Maintain a visible presence in classrooms, common spaces, and school events, building strong relationships with students and contributing to a positive school culture
• Coordinate responses to student behavior concerns, navigating complex situations with professionalism and sound judgment, and work with staff to ensure fair, consistent, and supportive outcomes aligned with school values and policies
• Support the implementation of restorative and developmentally appropriate approaches to student behavior that promote accountability, reflection, and connection
• Lead and manage projects and initiatives that advance school priorities and strengthen systems that support students, effectively navigating multiple priorities in a dynamic school environment

School and Community Partnerships

• Cultivate authentic, supportive relationships with students and families 
• Partner with outside organizations to support student success and strengthen connections between school and community
• Contribute as a member of the school and district leadership teams to the development and implementation of goals, priorities, and initiatives that foster a professional culture grounded in collaboration, reflection, and shared responsibility for student success
  

Additional duties may be assigned by the Principal or Superintendent in support of school and district priorities.

 

JOB ENVIRONMENT

Work takes place in classrooms and other building rooms/areas, including offices, auditorium, gym, lunchroom and hallways, within a school building setting, primarily indoors.  

PHYSICAL REQUIREMENTS

The physical demands described below are representative of those that must be met by an employee to successfully perform the essential functions of this job.  Reasonable accommodations may be made to enable individuals with disabilities to perform the essential 

functions.

• Requires sufficient vision to read printed documents and to view detail on a computer screen for extended periods.
• Requires frequent standing, walking, sitting, bending, and reaching, as well as carrying and occasionally lifting up to 30 lbs.  
• Ability to speak in an understandable voice with sufficient volume to be heard in normal conversation, on the telephone, and in the classroom.
• Ability to hear sounds clearly up to twenty feet.
• Travel among buildings may be required.

The Westwood Public Schools does not discriminate on the basis of race, color, religion, gender, gender expression, age, national origin, disability, marital status, sexual orientation, or military status.