Associate Director of College Counseling

Staff / Full-Time

The Winsor School, Boston, MA

 Associate Director of College Counseling

The Winsor School is an independent day school for academically promising and motivated girls in grades five through twelve. Winsor’s unique location in the city of Boston fosters an intellectual culture that mirrors the dynamic energy, climate and innovative spirit of the city.  Winsor enrolls approximately 450 students from more than 50 different local communities in and around Boston. Our diverse, vibrant community values intellectual curiosity, authentic engagement, and personal integrity and prepares young women to pursue their aspirations and contribute to the world. Winsor strives to create an environment of respect and inclusion.

The School is seeking an experienced, full-time associate director of college counseling to begin July 1, 2023. The associate director, which is a 12-month position, reports to the director of college counseling. Compelling applicants will embrace the School’s commitment to supporting students from diverse backgrounds and experiences in an atmosphere that is welcoming, responsive, realistic, and empathetic.

Major Functions and Responsibilities:

  • meeting one-on-one with approximately thirty students to help them identify and celebrate their unique strengths, areas of interest, academic and personal goals, and decision-making styles as they navigate the college search process
  • collaborating with students and families to build and modify realistic, highly individualized lists of colleges and universities and develop a strategic and responsive approach to application plans and outcomes
  • partnering with families to encourage students to explore opportunities, be strong self-advocates, manage expectations, weigh financial considerations, and select schools that are the best fit for them
  • providing appropriate support and guidance for students as they prepare their applications, particularly first-generation students, non-native English speakers, and those applying for financial aid
  • writing compelling and personalized letters of recommendation for approximately thirty students based on a thorough understanding of both the students and the School
  • advocating for students and articulating the strengths of the Winsor program to colleges and universities and, with the support of the director, to additional constituencies within the Winsor community
  • staying abreast of current issues and trends related to college admission, financial aid, and gap year programs
  • together with the director of college counseling, interpreting data as related to admission and application trends, testing, and projected outcomes
  • visiting and researching colleges to develop and maintain a working knowledge of individual colleges and universities, including unique scholarship opportunities and niche programs and also hosting college admissions representatives on campus or online
  • attending regional and national organizations for college admission counseling as well as other professional development opportunities
  • other duties as assigned, which may including advising a group of Upper School students, leading an independent learning seminar, or working with students in a club
  • adherence to general expectations regarding work hours, vacations, and to all other policies and procedures outlined in the School’s Faculty and Employee handbooks


  • bachelor’s degree is required; a master’s degree is preferred
  • a demonstrated commitment to equity and inclusion
  • significant experience in college counseling or college admissions
  • technological proficiency, especially Google Workspace and college counseling software systems
  • familiarity with the college and university financial aid process, scholarship opportunities, and athletic recruitment procedures



  • exceptional interpersonal skills
  • a genuine commitment to building relationships with students, families, and colleagues
  • excellent written and oral communication skills
  • ability to uphold professionalism, maintain confidentiality and discretion, and respond promptly to emails and phone calls
  • strong organizational skills, time management skills, and attention to detail
  • an ability to collaborate effectively
  • demonstrated integrity, adaptability, and reliability
  • a sense of humor



If you are interested in applying for this position, visit and submit an application for employment.


The Winsor School is an equal opportunity employer and will not discriminate against any application for employment on the basis of race, color, religion, gender, age, national origin, marital status, sexual orientation, genetic testing, veteran status, physical or mental disability, or on any other basis prohibited by law.



The Winsor School

Boston, MA
Elementary, Middle School, High School