Charlotte, North Carolina
Posted: 23-Feb-26
Location: Chicago, Illinois
Type: Full Time
Salary: $90,000 - $120,000
Categories:
Required Education:
About Wolcott College Prep
Wolcott College Prep is Chicagoland’s only independent college-prep high school serving bright students with learning differences, including dyslexia, dysgraphia, ADHD, and executive functioning challenges. With a 4:1 student-teacher ratio and 100% college acceptance rate, Wolcott is dedicated to empowering students with learning differences to reach their full potential through a strength-based approach to education.
Job Summary:
The Director of College Counseling oversees and manages all aspects of the college counseling program, developing comprehensive programming for students, parents, and faculty that recognizes and supports the needs of students with learning differences. This position serves as the primary guide for students and families through the college search, application, and transition process, with particular expertise in identifying colleges with appropriate support services and structured programs for students with learning differences and ADHD.
The Director of College Counseling is a senior administrator and serves as a key member of the executive administrative leadership team, working closely with the Head of School and Director of Student Services to provide leadership in the following areas:
College Counseling Program Leadership
- Develop and regularly review a comprehensive college counseling curriculum tailored to students with learning differences, beginning in 9th grade
- Create and maintain an annual calendar of college counseling educational programming for students and families
- Lead college counseling seminars, workshops, and individual/family meetings throughout the year
- Maintain current knowledge of colleges with structured support programs, coordinated services, and appropriate accommodations for students with learning differences
- Build and maintain strong relationships with college admissions representatives, particularly those from disability support services and structured programs
- Visit colleges regularly to evaluate programs and maintain relationships with admission officers and disability services coordinators
- Represent the school at professional meetings, college fairs (including CHOICES and NACAC)
- Maintain awareness of testing policies and accommodation procedures at various institutions
- Manage the college counseling departmental budget
- Collect and maintain college admissions and scholarship data for each graduating year
Individual Student Counseling and Support
- Develop balanced college lists with individual students, emphasizing appropriate levels of academic and learning support
- Assist students in identifying colleges that match their learning profiles, academic interests, and support needs
- Guide students through applications to structured support programs (such as SALT, LEP, etc.) when appropriate
- Conduct individual and small group college counseling sessions
- Review and provide feedback on college applications, essays, and supplemental materials
- Compose comprehensive letters of recommendation for each senior that contextualize the student's learning profile and growth
- Guide families on when and how to submit psychoeducational evaluations and accommodation documentation to colleges
- Coordinate the submission of all required school documents including transcripts, accommodation plans, and psychoeducational evaluations when requested
- Assist students and families with financial aid, scholarship processes, and understanding the costs of structured support programs
Collaboration and Communication
- Partner closely with the Director of Student Services, learning specialists, and faculty to understand each student's learning profile and support needs
- Educate students and families about the continuum of college support services, from basic accommodations to highly structured programs
- Educate students about standardized testing options, test-optional policies, and accommodations
- Facilitate conversations with families about disclosure of learning differences in the application process
- Work with faculty to develop skills for writing strong, supportive teacher recommendations
- Collaborate with the admissions team during the prospective student enrollment process
- Provide guidance to families on college transition planning, including summer programs and orientation
Professional Development and School Community
- Stay current on trends in college admissions, financial aid, and support services for students with learning differences
- Maintain active membership in professional organizations, including NACAC, IACAC, and organizations focused on LD/ADHD support in higher education
- Serve on the Administrative Leadership Team and participate in school-wide initiatives
- Provide professional development to faculty on college counseling topics and supporting student transitions
Wolcott College Prep seeks candidates who possess the following qualifications and personal qualities:
Educational Expertise and Knowledge
- Understanding of learning differences (dyslexia, dysgraphia, ADHD, executive functioning challenges) and how they impact college readiness and success
- Comprehensive knowledge of the continuum of college support services, from basic accommodations to highly structured programs
- Familiarity with psychoeducational evaluations and ability to interpret diagnostic information for college planning purposes
- Strong knowledge of college admissions processes, application platforms (Common App, etc.), and financial aid systems (FAFSA)
- Proficiency with college counseling technology platforms including Naviance, Common Application, and student information systems
- Understanding of standardized testing, test-optional policies, and accommodation procedures
Communication & Relationship Building Skills
- Genuine passion for working with students with learning differences and belief in their potential for college success
- Alignment with and enthusiasm for Wolcott's mission and strength-based philosophy
- Exceptional interpersonal skills and ability to build trust with students, families, and colleagues
- Strong verbal and written communication skills, including ability to give presentations to large and small groups
- Excellent organizational skills and attention to detail
- Ability to manage multiple priorities, meet deadlines, and work independently
- Professional demeanor, including tact, discretion, and a student-centered approach
- Ability to maintain confidentiality and handle sensitive information appropriately
- Genuine engagement with all levels of the school community and commitment to collaborative work
- Problem-solving skills and ability to adapt to changing circumstances
- Commitment to ongoing professional development and staying current in the field
Commitment to Diversity:
- A commitment and ability to foster an inclusive and diverse learning environment that embraces and celebrates differences, including differences in learning, race, ethnicity, socioeconomic background, religion, and sexual orientation.
Additional Requirements
- Ability to work flexible hours 1-2 times a month for occasional evenings for family programs or admissions programs
Educational Background and Experience
- Bachelor's degree required; Master's degree strongly preferred
- Minimum of 5 years of college counseling experience in secondary schools
- Knowledge of college programs and support services for students with learning differences and ADHD
- Experience working with selective college admissions processes
- Demonstrated experience working with diverse student populations and learning profiles
Physical Requirements:
- Talking: Exchange ideas and information by means of the spoken word to impart oral information to others accurately.
- Visual & Hearing Activity: Use telephone and computer on a daily basis. Ability to receive detailed information through oral and written communication.
- Ability to move around campus to interact with students, families, faculty, and staff
- Ability to attend off-campus events including college visits, fairs, and professional conferences
- Sedentary work involving extended periods at a computer for application review and correspondence
Compensation
Salary range: $90,000 - $120,000 commensurate with experience. Includes comprehensive benefits package.
Equal Employment Opportunity Statement
Wolcott College Prep is an equal opportunity employer and complies with all applicable anti-discrimination requirements set forth in the Illinois School Code as required for ISBE nonpublic school recognition, among other applicable state and federal antidiscrimination policies, in employment practices. Hiring, promotion, transfer, compensation, benefits, discipline, termination, and all other employment decisions are made without regard to an individual’s race, color, sex, gender, sexual orientation, religion, age, disability, national/ethnic origin, ancestry, citizenship/immigration status (provided the individual is authorized to work in the United States), marital status, or any other protected status. All employment decisions by Wolcott College Prep will be based on merit, qualifications, and abilities.