Head Of Community Jobs (NOW HIRING)

Our School, founded on Jewish values, is about who our children can become and how they can help others become who they might be. Because the world our children will create tomorrow is born in the School we build today, our mission is to educate our children so they can surpass us

The Chief of Staff to the Head of School serves as a strategic partner and force multiplier to the Head of School. This role is responsible for advancing institutional priorities by driving key initiatives, strengthening communication, and ensuring effective execution across the organization.

The Chief of Staff operates at a high level of trust and discretion, managing complex projects, preparing strategic communications, and anticipating needs in a fast-paced and dynamic environment. This individual helps translate vision into action, ensuring that the Head of School’s time, focus, and voice are leveraged for maximum impact across the school community.

This position reports directly to the Head of School.

This role requires exceptional writing and communication skills, strong strategic thinking, and the ability to manage ambiguity while moving work forward independently. The ideal candidate is proactive, highly organized, and able to operate with both big-picture perspective and attention to detail

Writing & Communications

• Draft and edit high-level communications including emails, speeches, presentations, and reports
• Capture and reflect the Head of School’s voice across internal and external audiences
• Ensure clarity, tone, and alignment in communications with faculty, parents, Trustees, and donors
• Partner with Communications and Advancement teams on messaging strategy

Project & Initiative Management

• Lead and drive key institutional initiatives on behalf of the Head of School
• Ensure accountability and follow-through on commitments and strategic priorities
• Take Head of School projects from concept through 70–80% completion, ensuring strong structure and momentum
• Develop  a project management system for timelines, coordinate stakeholders, and track deliverables
• Identify and resolve bottlenecks to ensure timely execution

Planning and Coordination 

• Anticipate needs, identify priorities, and think several steps ahead
• Prepare briefing materials, decision frameworks, and strategic analyses
• Work across academic, administrative, and operational teams to advance priorities
• Ensure alignment and follow-through on Head of School-led initiatives

Executive Organization

• Exceptional organization skills
• Maximize the Head of School’s impact by ensuring meetings are purposeful and well-prepared
• Prepare agendas, materials, and follow-up actions
• Track key priorities and ensure accountability across initiatives
• Identify opportunities to streamline processes and improve organizational effectiveness
• Track and manage follow-through on all key matters raised with or by the Head of School while ensuring timely resolution and closure
• Represent the HOS in select meetings, initiatives, and cross-functional discussions as appropriate

Research & Institutional Support

• Conduct research and analysis to inform decision-making and strategy
• Prepare reports, presentations, and background materials for internal and external use
• Support Board materials and leadership communications as needed
• Stay informed on trends and best practices in independent school leadership and education
• Other duties as assigned

• 3-7 years of progressively responsible experience in executive support, strategy, communications, project management, or organizational leadership roles.
• Exceptional writing and editing skills with the ability to adapt tone for multiple audiences
• Strong interpersonal skills and comfort working with senior leaders and diverse stakeholders
• Proactive, solution-oriented mindset with the ability to anticipate needs
• Demonstrated ability to manage complex projects and drive execution independently
• Strong analytical, strategic thinking, and problem-solving skills with the ability to synthesize complex information into actionable recommendations and leadership materialsHigh emotional intelligence, exceptional professional judgment, and the ability to handle confidential and sensitive matters with discretion
• Ability to operate effectively in a fast-paced environment with competing priorities
• Experience in education or mission-driven organizations preferred but not required
• Highly proficient with Mac, Google Workplace, and generative AI tools

Standard On-Campus Hours

Start: M - F by 7:30AM
End: M -Th 4:00PM, F 3:00PM
*All schedules are subject to change.

Salary Range: $95,000 - $130,000 (annually)

For a complete overview of our benefits, please visit the Employment page on our website.

Milken strives to be a nurturing, diverse and inclusive community. It is a vibrant academic home, drawing faculty and staff from the spectrum of faith, social and cultural backgrounds.