Jobs · Administrative · Connecticut

Administrative Assistant to the CFOO

Westover School · Middlebury, CT · 2 wk ago
AdministrativeFull-time

The Administrative Assistant to the CFOO plays a key role in supporting the operational and financial functions that keep Westover running smoothly. This position provides comprehensive administrative, clerical, and coordination support to the CFOO and the broader Operations Team, ensuring timely follow-up on projects, clear communication across departments, and efficient management of day-to-day logistics.

About the Role

The ideal candidate is highly organized, detail-oriented, and proactive—someone who enjoys managing a wide variety of administrative tasks, coordinating multi-step operational projects, and serving as a reliable point of coordination for the CFOO and campus operations.

Responsibilities

  • Provide direct administrative assistance to the CFOO, including calendar management, meeting scheduling, and document preparation.
  • Track and follow up on departmental tasks, projects, and deadlines to ensure timely completion.
  • Prepare correspondence, reports, and internal communications on behalf of the CFOO.
  • Maintain organized electronic and physical filing systems for operational and business office records.
  • Aid with vendor communications, contracts, and documentation management.
  • Support communication and logistics between departments such as Facilities, Housekeeping, Transportation, and Dining Services.
  • Monitor shared inboxes (e.g., transportation requests, maintenance requests) and route items to the appropriate staff for follow-up.
  • Assist in scheduling and tracking routine campus maintenance, event setup, and transportation coverage.
  • Cook up logistics for key school events such as opening days, graduation, and major community weekends.
  • Aid with transportation scheduling and coordination (airport runs, weekend trips, athletic travel).
  • Maintain transportation documentation, including driver rosters, licenses, and maintenance records.
  • Support the CFOO with budget tracking, invoice processing, and purchase order documentation.
  • Aid with data entry, reporting, and the preparation of materials for audits or board meetings.
  • Collaborate with other administrative offices to ensure smooth operations across campus.
  • Coordinate small to mid-size departmental or campus-wide projects, ensuring timelines, tasks, and stakeholders stay aligned.
  • Maintain project trackers and follow up with internal and external partners to ensure milestones are met.
  • Aid in developing and improving administrative workflows and operational processes.
  • Assist in implementing and rolling out new systems, tools, or operational initiatives led by the CFOO.

Qualifications

  • Minimum of 2–3 years of administrative support experience, preferably in a school or business office environment.
  • Strong organizational, communication, and project management skills, with the ability to prioritize and coordinate multiple tasks effectively.
  • Proficiency with Google Workspace and Microsoft Office; experience with scheduling, spreadsheets, and file management tools.
  • Valid and clean driver’s license required; willingness to obtain an A Endorsement upon hire.
  • A positive, service-oriented approach aligned with Westover’s mission and community values.

Skills

  • Organizational and time management skills.
  • Excellent written and verbal communication skills.
  • Ability to manage multiple tasks and projects simultaneously.
  • Proficiency with Google Workspace and Microsoft Office.
  • Experience with scheduling, spreadsheets, and file management tools.

Benefits

Competitive salary commensurate with experience.
Comprehensive benefits package including:
Health and vision insurance
Dental reimbursement
Health reimbursement arrangement
Life insurance
Retirement plan with employer contributions
Professional development support

Equal Opportunity Employer

We are committed to building a diverse and inclusive community and strongly encourage applications from candidates from historically marginalized or underrepresented backgrounds, as well as those with non-traditional career paths.

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