Dean of Enrollment Management

Cheshire Academy | Dean of Enrollment Management

Opportunity Statement | https : / / bit.ly / cheshiredem

About Cheshire Academy

Founded in 1794, Cheshire Academy is a coeducational boarding and day school serving grades 9-12 and postgraduate students. Located in Cheshire, Connecticut, we are committed to academic excellence, character development, and preparing students for success in college and beyond. Our beautiful 104-acre campus serves approximately 390 students from 13 states and 18 countries.

Position Summary

Cheshire Academy seeks a dynamic and strategic leader to serve as its inaugural Dean of Enrollment Management. This newly established role reflects the school's commitment to a holistic, institution-wide approach to enrollment that goes beyond traditional admission functions. The Dean of Enrollment Management will provide senior-level leadership, guiding enrollment strategy across the institution and serving as a key member of the senior leadership team with broad cross-functional responsibilities.

This position presents an exceptional opportunity to shape Cheshire Academy's enrollment philosophy and make a meaningful contribution to its long-term growth and success. The successful candidate will lead a comprehensive enrollment strategy for both domestic and international markets, working to enhance the school's position as a premier destination for students seeking challenging academics, cultural diversity, and preparation for global citizenship.

Salary Range

$150,000 - $180,000, commensurate with experience, with some upward flexibility for a highly experienced candidate.

How to Apply

Cheshire Academy has engaged DovetailED to lead this search. Interested candidates should email a cover letter (addressed to the Head of School's Executive Assistant, Marie Hastie), a resume, and a list of at least three professional references consolidated as a single PDF document to Zack Lehman at zack@dovetailedsourcing.com and Lynda Hamilton-Kirk at lynda@dovetailedsourcing.com.

Job description | https : / / bit.ly / cheshiredem