Job Title: Administrative Assistant to the Chief Financial and Operations Officer (CFOO)

Department: Business Office / Campus Operations

Reports to: Chief Finance and Operations Officer (CFOO)

Location: Middlebury, Connecticut

Position Type: Full-Time, 12-Month

About Us:

Westover School is an all-girls boarding and day school in Middlebury, Connecticut, with a mission to empower young women to lead lives of consequence. We are committed to fostering a diverse, inclusive, and globally minded community where students thrive academically and personally.

Westover School in Middlebury, CT, has engaged DovetailED to lead a search for an Administrative Assistant to the Chief Finance and Operations Officer (CFOO) to start as soon as possible. Interested candidates should review the Opportunity Statement and submit a cover letter, resume, and list of references as a consolidated PDF to Madison Sunley, Senior Recruiter at DovetailED Talent Sourcing, at madison@dovetailedsourcing.com            

Westover School Administrative Assistant to the CFOO Opportunity Statement Link: https://bit.ly/3VUwWMM

Job Summary:

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.

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 and Duties:

Administrative Support to CFOO

• 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.
• Assist with vendor communications, contracts, and documentation management.

Operations Coordination

• 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.
• Coordinate logistics for key school events such as opening days, graduation, and major community weekends.

Transportation and Logistics Support

• Assist with transportation scheduling and coordination (airport runs, weekend trips, athletic travel).
• Maintain transportation documentation, including driver rosters, licenses, and maintenance records.

Business Office and Administrative Projects

• Support the CFOO with budget tracking, invoice processing, and purchase order documentation.
• Assist 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.

Project and Process Management

• 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.
• Assist in developing and improving administrative workflows and operational processes.
• Support implementation and rollout of new systems, tools, or operational initiatives led by the CFOO.

Required Qualifications and Skills:

• 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.
• Professionalism, discretion, and the ability to handle confidential information appropriately.
• Valid and clean driver’s license required; willingness to obtain an A Endorsement upon hire.
• Positive, service-oriented approach aligned with Westover’s mission and community values.

Working Conditions:

• Primarily on campus, indoors and outdoors, in various operational settings
• Requires occasional evening or weekend work to support events or transportation needs

Physical Requirements:

• Ability to lift up to 25 lbs
• Must be able to walk across campus, climb stairs, and occasionally drive school vehicles
• May be required to work in inclement weather during transportation or outdoor event setup

Compensation and 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

Westover School in Middlebury, CT, has engaged DovetailED to lead a search for an Administrative Assistant to the Chief Finance and Operations Officer (CFOO) to start as soon as possible. Interested candidates should review the Opportunity Statement and submit a cover letter, resume, and list of references as a consolidated PDF to Madison Sunley, Senior Recruiter at DovetailED Talent Sourcing, at madison@dovetailedsourcing.com            

Westover School Administrative Assistant to the CFOO Opportunity Statement Link: https://bit.ly/3VUwWMM

EEO Statement:

Westover School is an Equal Opportunity Employer and does not discriminate based on race, color, religion, national origin, ancestry, citizenship status, age, disability, sex, marital status, veteran status, sexual orientation, gender identity or expression, genetic information, or any other characteristic protected by applicable law. 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.