Executive Assistant to the Head of School

Executive Assistant to the Head of School

ABOUT THE CHICAGO ACADEMY FOR THE ARTS

The Chicago Academy for the Arts (chicagoacademyforthearts.org) 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. (Note: The Chicago Academy for the Arts is a different school from “ChiArts”, a CPS school.)

Students at the Academy are characterized by an extraordinary sense of purpose and community. Most continue with the arts after high school: alumni include hit songwriters, Grammy Award nominees and winners, Broadway stars, internationally acclaimed dancers, and award-winning filmmakers and writers. Students also pursue degrees and careers outside of the arts. Many alumni are successful professionals in science, mathematics, technology, business, law, and medicine.

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.

Reporting directly to the Head of School, 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…