2026-27 Assistant Head of School

TrulyHired

Worcester (MA)

On-site

USD 110,000 - 170,000

Full time

4 days ago

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Benefits offered by this job

Dental insurance

Employee assistance program

Employee discount

Flexible spending account

Health insurance

Health savings account

Life insurance

Paid time off

Retirement plan

Vision insurance

Job summary

Worcester Cultural Academy Public Charter School is seeking an experienced Assistant Head of School to act as the Head of School's chief deputy—visible in classrooms, restorative circles, and family engagement. The role demands leadership across culture, instruction, and operations with a relentless focus on belonging and equity.

The role involves long days with after-hours events and weekend commitments as needed, and requires strategic thinking, data-informed decisions, and deep collaboration

Qualifications

Bachelor's degree required; Master's degree strongly preferred.
Massachusetts DESE license as Assistant Principal or Principal, or eligibility.
Meaningful classroom teaching experience with credibility with teachers.
Experience in school leadership, instructional coaching, or roles with student culture responsibility.
Deep knowledge of restorative practices and culturally competent engagement.
Ability to engage diverse families and communities with warmth and clarity.

Responsibilities

Serve as a genuine thought partner and co-leader to the Head of School.
Step into the Head of School role confidently when needed.
Contribute to school-wide strategic planning, goal-setting, and improvement.
Build a school culture that is high-expectation, supportive, and belonging-focused.
Collaborate with Head of School on staff hiring, onboarding, and team development.
Support school-wide systems and structures enabling students and staff to thrive.
Lead the school's restorative approach to culture and behavior.
Engage families and community partners with empathy and transparency.

Skills

Restorative practices

Leadership experience

Data-driven decisions

Stakeholder engagement

Instructional coaching

Curriculum knowledge K-7

English Learners experience

Education

Bachelor's degree

Master's degree in Education/School Leadership

Massachusetts DESE license eligible

Job description

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 neededContribute 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