2026-27 Assistant Head of School

2026-27 Assistant Head of School Old Sturbridge Academy Charter Public School & Worcester Cultural Academy Charter Public School Worcester Cultural Academy Charter Public School - Worcester, Massachusetts Job Details

Job ID:

5656447

Application Deadline:

Posted until filled

Posted:

Apr 20, 2026 12:00 AM (UTC)

Starting Date:

Aug 3, 2026 Job Description Worcester Cultural Academy Public Charter School is seeking an experienced, dynamic, and deeply committed Assistant Head of School to serve as the Head of School's true second-in-command. This is not a supporting role — it is a leadership role in every sense. We are looking for someone who is equally at home in a classroom conversation about instruction and a restorative circle with a student and family. You will be a visible, trusted presence for students, staff, and families, and a thought partner and co-leader for the Head of School. We welcome culturally competent candidates who reflect the cultural diversity of our Worcester community. We want to be honest with prospective candidates: this role is demanding in ways that are hard to fully capture in a job description. You will wear many hats, move between competing priorities with speed and grace, and be asked to show up fully for students, families, and staff every single day. The pace is real, the stakes are high, and the work is deeply meaningful. If that is the kind of leadership role you have been looking for, we want to hear from you. The standard school day runs 7:30am-4:00pm, but this is a school leadership role and carries expectations that extend beyond those hours. Evening family events, school functions, and occasional weekend commitments are a regular part of the position. As an administrator, you are a visible representative of WCA's mission and community — and that responsibility does not clock out at the end of the school day. What You'll Do School Leadership and Partnership Serve as a genuine thought partner and co-leader to the Head of School, sharing responsibility for the culture, operations, and academic life of the school Step into the Head of School role confidently and capably when needed Contribute to school-wide strategic planning, goal-setting, and continuous improvement Build and sustain a school culture that is high-expectation, deeply supportive, and rooted in belonging for every student and adult Collaborate with the Head of School on staff hiring, onboarding, and team development Support the development and implementation of school-wide systems and structures that allow students and staff to thrive Curriculum and Instruction Maintain a strong working knowledge of effective teaching practices across grades K-7, with enough depth to speak credibly and specifically with teachers about their craft Conduct regular classroom walkthroughs and provide meaningful, actionable feedback to teachers in support of their growth Support the school's implementation of EL Education, including Learning Expeditions, portfolio-based assessment, and student-led conferences Collaborate with teachers on lesson planning, unit design, and instructional problem-solving Work toward building the capacity to conduct formal teacher evaluations, with the goal of taking on that responsibility as the role evolves Use student data — including iReady, MCAS, and progress monitoring — to identify trends, support teachers, and drive school-wide instructional decisions Student Culture and Behavior Lead the school's approach to student culture and behavior with a restorative practices framework at the center, blending traditional consequences when appropriate and necessary Build genuine, trusting relationships with students across all grade levels — being known, visible, and approachable every day Respond to behavioral incidents with consistency, fairness, cultural competence, and a genuine commitment to repairing relationships and restoring students to learning Develop and implement proactive systems that prevent escalation and build students' social-emotional skills over time Maintain clear and organized documentation of behavioral incidents, patterns, and outcomes Family and Community Engagement Serve as a primary point of contact for families navigating behavioral concerns, conflicts, or difficult conversations — approaching every interaction with empathy, honesty, and cultural humility Build authentic relationships with families across linguistic and cultural differences, ensuring every family feels known and respected Communicate proactively with families about both concerns and celebrations Partner with community organizations and support services to connect families with resources beyond the school Operational and Administrative Leadership Support the day-to-day operational needs of the school, stepping in wherever leadership is needed Assist with scheduling, coverage, safety procedures, and other administrative functions as needed Contribute to a school environment where staff feel supported, seen, and set up to do their best work Take on responsibilities as they emerge — this role will evolve as our school grows, and we need someone who grows with it What You Bring Bachelor's degree required; Master's degree in Education, School Leadership, or a related field strongly preferred Massachusetts DESE license as an Assistant Principal or Principal, or eligibility for licensure Meaningful classroom teaching experience — you have been in the room and you bring that credibility to every conversation with teachers Experience in school leadership, instructional coaching, or a role with significant responsibility for student culture and behavior Deep knowledge of restorative practices and the skill to implement them authentically with students, families, and staff Strong instructional knowledge across elementary and middle grades, with the ability to engage teachers in substantive conversations about their craft Experience working with English Language Learners and students with IEPs in diverse school communities Exceptional relationship-building skills with students, families, and colleagues across a range of cultural and linguistic backgrounds The ability to hold firm and make difficult decisions while remaining warm, fair, and trusted Comfort with data — using it to understand what students and teachers need and to drive action Extraordinary flexibility, resilience, and the capacity to hold many things at once without losing sight of what matters most A genuine belief in this school's mission and a desire to be part of building it for the long term

Benefits:

Dental insurance Employee assistance program Employee discount Flexible spending account Health insurance Health savings account Life insurance Paid time off Retirement plan Vision insurance

Work Location:

In person Interested candidates may apply here: https://www.surveymonkey.com/r/5XF8PK7 (you might need to copy & paste)

Position Type:

Full-time