Associate Director of Admission

About Us

Westover School is a vibrant independent boarding and day school dedicated to empowering young women through rigorous academics, leadership opportunities, and a supportive community. Our mission-centered admission process is essential to sustaining a diverse, engaged, and thriving student body.

The Office of Admission plays a critical role in shaping the future of Westover by identifying, recruiting, and enrolling students who will contribute meaningfully to the academic and community life of the school.

Westover School in Middlebury, CT has engaged Dovetail ED to lead a search for an Associate Director of Admission to start July 1, 2026. 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 Dovetail ED Talent Sourcing, at m

This role requires a high level of initiative, strong interpersonal skills, comfort with extensive travel, and the ability to balance strategic planning with day-to-day execution in a fast-paced, student- and family-centered environment.

• Serve as a primary recruiter for assigned geographic territories, including setting recruitment goals, monitoring metrics, and executing strategies to increase yield from target markets.
• Travel extensively (approximately 50% or more of the time) to represent Westover at conferences, school fairs, and recruitment events, coordinating with other Westover offices and partner boarding schools as appropriate.
• Cultivate and maintain relationships with educational consultants, placement directors, and school partners.
• Interview prospective students and families and serve as a key ambassador for Westover’s mission and values.

• Enter interview notes, contact records, communications with prospective families, and travel details into the admission database in a timely and accurate manner.
• Utilize and maintain database systems (including Blackbaud K–12) to track recruitment activity, manage communication, and support enrollment goals.
• Apply market research, demographic data, and enrollment trends to inform recruitment strategies.

• Collaborate with the Admission team on all aspects of Westover’s campus visit program.
• Strategize, plan, and execute admission events and initiatives in collaboration with the Office of Admission.
• Support broader enrollment management initiatives as needed.

• Partner with colleagues across campus to support recruitment efforts and ensure a cohesive admission experience for prospective families.
• Educate families on the financial aid process in collaboration with the enrollment and business offices.
• Contribute positively to a collaborative, professional, and mission-aligned admission team culture.

• Mid-level recruitment experience at an independent boarding school required.
• Exceptional written, verbal, and interpersonal communication skills.
• Strong analytical, organizational, and technological skills.
• Understanding of market research, demographics, and student recruitment strategies.
• Basic financial acumen to effectively communicate about the financial aid process.
• Experience with database management systems; familiarity with Blackbaud K–12 strongly preferred.
• Ability to multitask, remain flexible, and work effectively in a fast-paced, customer-centric environment.

This role involves extensive travel, including evenings and weekends, particularly during peak recruitment seasons. Work includes extended periods of sitting, computer use, data entry, and standing or walking during tours, fairs, and events. Frequent stair use and occasional lifting are required.

• Ability to travel frequently and work flexible hours.
• Ability to stand and walk for extended periods during tours, visits, and recruitment events.
• Ability to lift and carry materials related to travel and events.
• Ability to work at a computer and communicate effectively in person, by phone, and electronically.