Assistant/Associate Dean of College Counseling at Cheshire Academy – Cheshire, Connecticut

Description

Reports to Dean of College Counseling

10-month, full-time exempt position

Please include a cover letter to be considered

Cheshire Academy seeks an enthusiastic, student-centered, and highly qualified professional to join our College Counseling team as an Assistant/Associate Dean of College Counseling. Reporting to the Dean of College Counseling, this role is ideal for a collaborative and organized educator who is passionate about guiding students and families through the college search and application process while fully engaging in the life of a vibrant independent school community.

FUNCTION: The Associate Dean of College Counseling serves as a primary college counselor for a diverse caseload of students and plays an active role in shaping and delivering Cheshire Academy’s comprehensive college counseling program. The successful candidate will bring strong interpersonal skills, exceptional attention to detail, and a deep understanding of selective college admissions.

The level of appointment (Assistant or Associate) will be determined based on experience and qualifications.

PRIMARY RESPONSIBILITIES

• Serve as the primary college counselor for approximately 30–40 students in grades 10–12 and postgraduates, providing individualized guidance throughout the college planning process.
• Advise and support students and their parent(s)/guardian(s) on all aspects of college exploration, selection, and application, including course planning, standardized testing, essays, and decision-making.
• Write personal, detailed, and compelling letters of recommendation that reflect a deep knowledge of each student’s academic strengths, character, and extracurricular involvement.
• Actively contribute to college counseling presentations, workshops, and programs, including select evening and weekend events.
• Visit college campuses during the academic year and summer to maintain current knowledge of institutions and admissions trends.
• Participate fully in the life of a residential boarding school, including engagement during and after school hours.
• Assist the Coordinator of Testing with all standardized testing programs, including PSAT, SAT, and practice SAT/ACT administrations.
• Attend and represent Cheshire Academy at professional conferences and admissions events.

EDUCATION AND EXPERIENCE

• Bachelor’s degree required; master’s degree preferred.
• Minimum of two years of experience in selective college admissions and/or independent school college counseling.

SKILLS AND ABILITIES

• Outstanding organizational, time-management, and communication skills (written and oral).
• Demonstrated ability to work collaboratively and effectively with a diverse community of students, families, faculty, and administrators.
• A student-focused, ethical, and empathetic approach to college counseling.
• Clear commitment to belonging, inclusion, and community building.