Chief of Staff to the Head of School

Our MissionOur 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 usPosition OverviewThe 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 detailResponsibilitiesWriting & CommunicationsDraft and edit high-level communications including emails, speeches, presentations, and reportsCapture and reflect the Head of School’s voice across internal and external audiencesEnsure clarity, tone, and alignment in communications with faculty, parents, Trustees, and donorsPartner with Communications and Advancement teams on messaging strategyProject & Initiative ManagementLead and drive key institutional initiatives on behalf of the Head of SchoolEnsure accountability and follow-through on commitments and strategic prioritiesTake Head of School projects from concept through 70–80% completion, ensuring strong structure and momentumDevelop a project management system for timelines, coordinate stakeholders, and track deliverablesIdentify and resolve bottlenecks to ensure timely executionPlanning and CoordinationAnticipate needs, identify priorities, and think several steps aheadPrepare briefing materials, decision frameworks, and strategic analysesWork across academic, administrative, and operational teams to advance prioritiesEnsure alignment and follow-through on Head of School-led initiativesExecutive OrganizationExceptional organization skillsMaximize the Head of School’s impact by ensuring meetings are purposeful and well-preparedPrepare agendas, materials, and follow-up actionsTrack key priorities and ensure accountability across initiativesIdentify opportunities to streamline processes and improve organizational effectivenessTrack and manage follow-through on all key matters raised with or by the Head of School while ensuring timely resolution and closureRepresent the HOS in select meetings, initiatives, and cross-functional discussions as appropriateResearch & Institutional SupportConduct research and analysis to inform decision-making and strategyPrepare reports, presentations, and background materials for internal and external useSupport Board materials and leadership communications as neededStay informed on trends and best practices in independent school leadership and educationOther duties as assignedQualifications3-7 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 audiencesStrong interpersonal skills and comfort working with senior leaders and diverse stakeholdersProactive, solution-oriented mindset with the ability to anticipate needsDemonstrated ability to manage complex projects and drive execution independentlyStrong 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 discretionAbility to operate effectively in a fast-paced environment with competing prioritiesExperience in education or mission-driven organizations preferred but not requiredHighly proficient with Mac, Google Workplace, and generative AI toolsStandard On-Campus HoursStart: M - F by 7:30AMEnd: M -Th 4:00PM, F 3:00PMAll 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. #J-18808-Ljbffr