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Windward School

Dean of College Counseling

College Counseling · Los Angeles, California
Department College Counseling
Employment Type Active Full Time
Minimum Experience Experienced

Windward School is a co-educational, independent, college-preparatory day school enrolling students in grades 7-12. Located in West Los Angeles, Windward draws its student body from the diverse population of Los Angeles. 

Windward is seeking a Dean of College Counseling to join its dynamic College Counseling team: two full-time Deans of College Counseling, two part-time College Counselors, and a College Counseling Coordinator. 

As an integral member of the administrative team, the Dean will help lead the college search process for both students and parents. The Dean will assume a pivotal role in guiding students and in helping them take stock of their academic and extracurricular talents and interests. This includes counseling families through general grade-level meetings and formal one-on-one sessions on the intricacies of the college application and selection process. 

As an expansion of the team, the ideal candidate will be a highly engaged member of our inclusive and nurturing community, endeavoring to understand, participate in, and communicate to outside groups the vibrant life of Windward School.

Windward School has a unique structure comprised of three distinct divisions: Middle School (grades 7,8), Prep (grades 9,10) and Collegiate (grades 11,12). Each division has a Director, Associate Director, Dean of Students and Counselor in an effort to ensure that every student feels known. The three Deans of College Counseling jointly direct the department and are members of the Collegiate Division, reporting equally to the Assistant Head of School. The Deans of College Counseling also work closely with the Prep Division to support their programming and counseling.


College Counseling/School Responsibilities:

  • Manage a comprehensive college counseling program as one of three Deans in a collaborative model of leadership

  • Manage a caseload of seniors, juniors and sophomores as they navigate all aspects of the college counseling process: student and family meetings, activity planning, summer program selection, college application and essay review, application processing, test prep advisement and strategies, interview prep, college list making, etc.

  • Write a letter of recommendation for each senior counselee

  • Advise and schedule coursework for rising juniors and seniors

  • Host college representatives visiting Windward School

  • Co-plan and execute a variety of college counseling events

  • Chaperone a multi-day East Coast college trip for juniors

  • Attend fly-in opportunities to visit colleges and universities 

  • Maintain communication and cultivate relationships with admission officers

  • Advise faculty on recommendation writing process

  • Coordinate office logistics with College Counseling Coordinator 

  • Contribute to a weekly newsletter and special projects

  • Represent Windward School at regional and national conferences

  • Present at Parent Guild, Board and Faculty meetings, as requested

  • Attend grade-level retreats, as assigned


Ideal Candidate will have:

  • Minimum 8-10 years experience in college counseling and/or college admissions

  • Understanding of highly selective college admission

  • Commitment to diversity, equity and inclusion

  • Values including teamwork, organization, sense of humor, attention to detail, accountability, flexibility, and positive attitude

  • Knowledge of independent school philosophy and culture

  • Demonstrated ability to balance independence while working in a highly collaborative environment

  • Ability to work well one-on-one with high school students

  • Exceptional written, oral, interpersonal, and presentation skills

  • Proficiency with technology and online resources

  • Willingness to work some nights and weekends

  • Bachelor’s degree required/Master’s degree preferred


We offer competitive compensation and benefits, including:

  • Medical, dental, vision insurance

  • Paid Holidays, Vacation and Wellness days

  • Retirement Plan, including up to 6% employer match

  • School-paid Life and Disability Insurance

  • Flexible Spending Account Plans

  • Annual $2,000 FlexCheck

  • Annual $2,000 Lunch Allowance

  • Access to Peak Performance Center to promote physical and mental health

  • Employee Assistance Program

  • Tuition Remission

  • Nurturing, supportive and inclusive community

  • And much more!


For more information about Windward School, see our website:


To Apply:  Please email your resume, cover letter and a sample letter of recommendation to



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  • Location
    Los Angeles, California
  • Department
    College Counseling
  • Employment Type
    Active Full Time
  • Minimum Experience