Director of Secondary School Advising

Eaglebrook School, Deerfield, MA

Accredited by AISNE


Eaglebrook is a junior boarding and day school for boys in grades six, seven, eight, and nine, located in Deerfield, Massachusetts. Founded in 1922, Eaglebrook’s vision is to help each student develop his unique gifts during the important middle school years, and our mission is to meet boys where they are in their development and to encourage them to build self-confidence through success. Eaglebrook offers a rich and diverse curriculum geared toward the learning styles of middle school boys.

The Position

The Director of Secondary School Advising assists the Sixth Form (ninth grade) students, and Fifth Form (eighth grade) students and their parents in securing acceptance at the secondary school(s) that is (are) most appropriate to the abilities, interests, and needs of the student. The Director also hosts many secondary school admission representatives who visit Eaglebrook in order to provide updated information about academic and physical changes at the secondary school and who may meet directly with groups of Sixth Form students who might have an interest in that school. The Director works collaboratively with the Associate Director to coordinate SSAT testing. The Director of Secondary School Advising reports to and works closely with the Head of School.

Major Duties and Responsibilities

  • Placement of Sixth Form students, with the support of Associate Director, including all aspects of the process from developing an initial list of appropriate school choices, supporting the interview and school visit process, teacher recommendations, writing of Sixth Form appraisals, and completion of applications for admission including final paperwork needed from the school at the end of the year.
  • Develops a strong understanding of each student through a comprehensive review of academic reports, admission file summaries, teacher feedback including collaboration with the Director of Academic Skills to understand WISC testing on file, standardized testing, and individual meetings with students.
  • Establishes and maintains close relations with Admissions Directors at secondary schools through hosting, coordination, communication, and off-site visits.
  • Works closely with Fifth Form students to prepare them for the secondary school process in their Sixth Form year, including a review of their course schedule, athletics, extracurricular activities, and co-coordinating a secondary school fair each spring.
  • Works with the Associate Director to administer SSAT Testing and management of test results.
  • Collaborates with the Associate Director and Administrative Assistant to achieve positive outcomes for students.
  • Works with families and students during March break to support school decisions.
  • Oversees the efficacy and efficiency of the Secondary School Advising Office.
  • Attends and participates in all faculty meetings, administrative council meetings, program management team meetings, administrative retreats, and school events, and trips.
  • Serves as a teacher and coach during the school year.
  • Covers a table in the Dining Hall.
  • Participates in assigned weekend duty shifts and the on/off roster.


  • Knowledgeable about the secondary school placement process, whether from a placement or admissions perspective
  • Committed to developing positive relationships with students and parents; ability to work effectively with a variety of constituents
  • Detail-oriented and organized
  • Outstanding written, communication and presentation skills
  • Proven ability to work both independently and collaboratively
  • Self-starter and solution-oriented
  • Steward for diversity, equity, and inclusion in all facets of school life
  • Strong project management and organizational skills
  • Technology skills and ability to implement technological solutions
  • Valid driver’s license and successful completion of a CORE background check
  • Willingness to travel at times to attend conferences and visit secondary schools



  • Bachelor’s Degree and a minimum of five years of leadership/management experience


Successful applicants should have a high level of comfort with computers, copiers, and printers. Proficiency with Office 365 and G Suite is required.

Qualities of an Eaglebrook Director of Secondary School Advising

  • Approachable
  • Collaborative
  • Communicative
  • Empathetic
  • Flexible
  • Focused
  • Growth mindset
  • Listener
  • Open-minded
  • Patient
  • Positive
  • Proactive
  • Relational
  • Reliable
  • Responsive
  • Self-aware






Please email a cover letter and resume to Sharon Calvo, Assistant to the Head of Sch

  • advising
  • Director