Executive Assistant to the Headmaster

Job Description

Job Description

Ridgeview Classical Schools is seeking an Executive Assistant to the Headmaster who can help manage the daily rhythm of the school - protecting the Headmaster’s time and attention, keeping the school’s events and traditions running well, and making sure the many moving pieces of a school year land where and when they should. This is an administrator-level position.

The ideal candidate is someone who takes genuine pleasure in bringing order to complexity, who communicates warmly and clearly and who understands that the small details of a school year are part of what makes a school feel like a community rather than an institution.

Key Responsibilities

Executive Support

• Manage the Headmaster’s calendar, including meetings, teaching, and travel.
• Anticipate scheduling conflicts and recurring seasonal demands before they become urgent, using the school’s annual rhythm (hiring cycles, evaluation season, events) as a guide.
• Maintain the Headmaster’s running to-do list, including seasonal and summer priorities, and help track follow-up items after key meetings.
• Support the Headmaster in developing the school's donor relations efforts: scheduling donor meetings and maintaining documentation of contacts, outreach dates, and the nature of each ask.
• Maintain the Headmaster's supply inventory, ordering supplies as needed.
• Submit receipts in a timely fashion and assist the Headmaster with expense tracking as needed.
• Provide Human Resources support to the Headmaster and/or Business Office as needed.

Communications

• Draft, compile, and distribute the weekly Nuntius (community newsletter), coordinating submissions and meeting the weekly deadline.
• Draft and distribute all-school communications, including general information, closure announcements, etc.
• Prepare materials and notes for Headmaster’s Coffees, faculty meetings, admin meetings, and board meetings; distribute notes and track follow-up items.
• Serve as a primary point of contact for parents, faculty, and vendors on matters related to the Headmaster’s office.

School Events & Traditions

• Coordinate with other administration in the planning and execution of signature Ridgeview events across the school year, including but not limited to Back to School Night, First Responders’ Day, Valborgsmassoafton, the Senior Banquet, EOY Awards Assemblies, the Field Day Picnic, and Graduation.
• Manage event logistics, including venues, catering, vendors, supplies, and volunteer coordination, tracking tasks for each event using Asana or a similar project management software.
• Plan and coordinate school catering for events, teacher training, and parent-teacher conferences.
• Prepare and set up for the weekly and monthly parent book group meetings.

Talent Pipeline, Recruitment, Hiring, & Onboarding

• Develop and maintain a recruitment pipeline of prospective faculty, including writing and designing three recruitment newsletters per year to keep candidates warm and engaged.
• Support the annual faculty hiring cycle: posting positions, processing applications, and scheduling interviews and mock teaches.
• Maintain organized hiring records and applicant tracking for each open position.
• Assist with new faculty and staff onboarding.

Qualifications

Required

• Genuine warmth and professionalism in working with parents, faculty, and students.
• Strong organizational instincts — the ability to track many concurrent, seasonal projects without losing the thread.
• Excellent written communication; comfortable drafting community-facing correspondence. Applicants will be asked to submit a writing sample.
• Sound judgment and discretion in handling confidential or sensitive information.
• Proficiency with standard office and scheduling tools (Microsoft 365); willingness to learn school systems such as PowerSchool, Asana, and FMX.

Preferred

• Prior experience in a school, nonprofit, or similarly relationship-driven organization.
• Familiarity with or enthusiasm for classical education.
• Event planning or project coordination experience.
• Previous Executive Assistant experience.