Executive Assistant to the Head of School

About The Chicago Academy for the Arts

The Chicago Academy for the Arts is Illinois' premier independent high school for visual and performing arts. The Academy's educational model is co-curricular: students engage in rigorous academic classes alongside professional-level training in dance, filmmaking, animation, writing, music, musical theatre, theatre, or visual arts. Students at the Academy are characterized by an extraordinary sense of purpose and community. Our working environment is inspired and authentically mission-driven. This is an extraordinary opportunity to play a meaningful role in a school that routinely transforms the lives of its students. Simply put: this work matters.

Position Summary

The Executive Assistant to the Head of School provides high-level, confidential, and professional administrative support to the Head of School and serves as the operational center of the Head's Office. This role is critical to the smooth functioning of the school's leadership, coordinating a complex calendar, managing communications, supporting Board of Trustees activities, and ensuring the Head of School can focus on the Academy's students, faculty, and strategic priorities. This position calls for a proactive, organized, and discreet professional who can anticipate needs, manage competing priorities with grace, and represent the Academy with warmth and professionalism to all constituents. The ideal candidate brings exceptional communication and organizational skills, sound judgment, and a genuine enthusiasm for arts education.

Key Responsibilities

Calendar & Time Management

• Manage a complex, high-priority calendar for the Head of School, scheduling meetings and engagements in alignment with school priorities and the Head's strategic focus areas.
• Anticipate scheduling needs, proactively resolve conflicts, and protect time for preparation, reflection, and key institutional commitments.
• Coordinate scheduling across the Head's Office and with members of the Senior Leadership Team.
• Assist with annual and quarterly calendar planning, including recurring leadership meetings, Board meetings, and school-wide events.

Communications & Correspondence

• Draft, edit, and manage a wide range of professional communications, including all-school messages, Board correspondence, donor thank-you notes, speaking remarks, and external correspondence on behalf of the Head of School.
• Maintain a Communications Calendar tracking all annually recurring correspondence, presentations, and deadlines to ensure timely and strategic outreach.
• Screen and route phone calls, emails, and visitor inquiries with professionalism and warmth; serve as a primary point of contact for the Head's Office.
• Maintain organized archives of past communications, remarks, and presentations for reference and continuity.

Board of Trustees Support

• Serve as the primary staff liaison to the Board of Trustees and Board subcommittees, coordinating all meeting logistics, agendas, materials preparation, and follow-up.
• Record and distribute accurate minutes for full Board and committee meetings; maintain rosters, files, and committee records.
• Support planning and on-site execution of all in-person Board meetings and related events.
• Maintain the Board handbook and ensure Board members have timely access to all relevant documents and communications.

Office & Administrative Operations

• Develop, document, and continuously improve processes for all recurring administrative activities, including meeting preparation, mail distribution, reimbursements, credit card reconciliation, and supply management.
• Coordinate travel arrangements for the Head of School, including flights, hotels, ground transportation, and detailed itineraries.
• Manage expense reporting and budget tracking for the Head's Office.
• Maintain well-organized digital and physical filing systems to support institutional continuity and efficiency.

Events & Stakeholder Engagement

• Assist in the planning and execution of events hosted by the Head's Office, including leadership gatherings, donor cultivation events, alumni receptions, and school celebrations.
• Coordinate with the Advancement team to prepare the Head of School for donor meetings, ensuring timely briefing materials and appropriate follow-up.
• Help ensure the Head of School's meaningful presence at student performances, exhibitions, and key school milestones.
• Greet and host guests of the Head's Office with a welcoming and professional presence.

Cross-Departmental Collaboration

• Build strong working relationships with colleagues across all departments, including Advancement, Finance, Admissions, and the arts and academic departments.
• Support communication and coordination between the Head's Office and all school departments to ensure alignment on institutional priorities and smooth day-to-day operations.

Qualifications

Required:

• Bachelor's degree, or equivalent combination of education and experience.
• Experience as an executive assistant, chief of staff, or administrative professional.
• World-class written and verbal communication skills, with demonstrated ability to draft professional correspondence, presentations, and remarks.
• Outstanding organizational skills and meticulous attention to detail, with proven ability to manage multiple competing priorities under pressure.
• Demonstrated ability to handle sensitive information with strict confidentiality and sound judgment.
• Proficiency with Google Workspace (Docs, Sheets, Slides, Calendar, Drive) and Microsoft Office Suite.
• An engaging personality and ability to work effectively both independently and within a team-oriented environment.
• Ability to work effectively and calmly in a fast-paced, dynamic school environment.

Preferred:

• Experience in an independent school, arts organization, or other mission-driven nonprofit.
• Experience supporting a Board of Trustees or nonprofit governance body.
• Working knowledge of Salesforce or similar CRM/database tools.
• Passion for the arts and enthusiasm for the Academy's mission.

Core Competencies

• Professionalism and discretion — model the highest standards of integrity and confidentiality.
• Communication excellence — clear, warm, and precise in all written and verbal interactions.
• Proactive problem-solving — identifies challenges early and acts with initiative.
• Collaborative spirit — trusted by colleagues at all levels of the institution.
• Adaptability — navigates a dynamic school calendar and shifting priorities with poise.
• Commitment to mission — brings genuine enthusiasm for arts education and student success.

Compensation and Benefits

The salary for this position will begin at $50,000, commensurate with experience and qualifications. Full-time employees have access to medical and dental insurance, ancillary insurance, and a 403(b) matching program, along with generous paid time off and access to Academy performances, exhibitions, and artistic programming.

How to Apply

Interested candidates are invited to submit the following to employment@chicagoartsacadey.org (no calls, please):

• A cover letter describing your interest in The Chicago Academy for the Arts and the ways your experience prepares you for this role.
• A current résumé.
• Three professional references (references will not be contacted without prior notification).

The Chicago Academy for the Arts is an equal opportunity employer committed to building a culturally diverse community. All qualified applicants — regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, disability status, protected veteran status, or any other characteristic protected by law — are strongly encouraged to apply.

Key skills/competency

• Executive Assistant
• Calendar Management
• Communication
• Board Relations
• Administrative Operations
• Event Planning
• Confidentiality
• Google Workspace
• Microsoft Office
• Arts Education