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Thank you for your interest in a career with Winston.

At The Winston School San Antonio, we strive to provide the optimal environment for every student to learn, grow, and uncover their unique talents. Our success in achieving this goal is made possible by our outstanding faculty. At Winston, the dedication and passion of our faculty, staff, and administration make it possible for our students to achieve excellence every day.

Here is a list of available positions:

section 3

College Counselor


Job Title: College Counselor
Classification: Staff
FLSA Status: Exempt
Supervisor: Dean of Faculty

The College Counselor serves Winston students and families by providing a program that focuses on the major aspects of the college planning and placement process. With a goal of 100% college acceptance, this position directs a program of activities to assist students with college planning including academic preparation for college, meeting both graduation and college acceptance requirements, college searches, school and financial aid applications, scholarship searches, testing, recommendations, and transition to college.


Provide Individualized College Counseling:

  • Meet with 9th-12th grade students, individually and in groups to discuss the college admission timeline.
  • Provide personalized support to seniors, assisting with college list development, application essay review, and application(s) review.
  • Conduct annual individual meetings with students to craft a comprehensive four-year academic plan and address any academic challenges.
  • Conduct transcript reviews to ensure students are following appropriate course plans and will meet graduation requirements. 
  • Craft compelling letters of recommendation for each student, showcasing their academic achievements and personal attributes to prospective colleges.

Build College & University Relations:

  • Develop and deliver workshops and webinars addressing topics in the college admission process, such as college essay writing, academic accommodations, testing, financial aid, and Common Applications.
  • Actively participate in professional development activities such as admission representative visits to campus, national conferences, and/or regional workshops, to stay abreast of best practices in college admissions counseling.
  • Keep current on issues and trends in college admission, higher education, and testing, stay up-to-date with specific colleges, and maintain membership in professional organizations including NACAC, TACAC, and ACCIS. 
  • Cultivate relationships with college admissions representatives, including but not limited to those that offer learning support programs.

Oversee Standardized Testing:

  • Coordinate the program and calendar of all standardized testing for students (including PSAT, Pre-ACT, SAT, ACT), including scheduling test dates, registering students, and preparing accommodation requests, arranging for special prep sessions, administering the tests, and providing pre- and post-test counseling. 
  • Coordinate and schedule students to take the TSI Exam and subsequently oversee their dual-credit online course registration and completion.

Provide Alumni Support:

  • Oversee the Winston CARES Program and serve as the touchstone for participants (the program is to provide additional support to graduating Seniors as they become WSSA Alumni beginning their college/career journey. Students must opt-in at the time of enrollment.)

  • Provide students with positive reinforcement and positive redirection in accordance with Winston’s Employee Handbook.
  • Agree to uphold the mission of The Winston School San Antonio. 
  • Maintain strict confidentiality of all student and family information and documents in accordance with HIPAA and FERPA.
  • Abide by all requirements, policies, and standards of conduct as stated in the Winston Employee Handbook, Winston Family Handbook, and job offer letter.
  • Maintain appropriate accreditation data for current accrediting agencies, including but not limited to ISAS.
  • Participate in team meetings, professional development, and in-service training.
  • Maintain certification credentials and licensing as appropriate.
  • Take all necessary precautions to protect the safety of staff, students, and families; equipment; materials, and the facility.
  • Perform other duties as assigned, including chaperoning, participation on field trips, assisting with and/or participation in school special events (such as Field Day, Athletic Banquet, Annual Alumni event, school dances, etc.), and other activities or tasks, that may include evenings and weekends, not listed in this job description but requested by Supervisor, Director, or Head of School.
  • Bachelor’s degree and a minimum of five to seven years of experience in college counseling and/or college admissions; Master’s degree preferred.
  • Familiarity with Naviance or Scoir, CommonApp, and Slate.
  • Certified School Counselor or Teacher, and/or eligible for certification.
  • Familiarity with the Family Education Rights and Privacy Act (FERPA).
  • Highly developed verbal and written communication skills.
  • Ability to set priorities, and complete work promptly, often working with multiple competing deadlines.
  • Able to effectively engage diverse parents/ guardians with varied communication styles, levels of skill, and experience to support their child's education experience.
  • Able to work effectively as a collaborative member of an interdisciplinary team, and be a team player who contributes beyond the college counseling program.
  • Able to stand, move throughout the campus, operate a computer, ascend/descend stairs, stoop, kneel and crouch.
  • Able to lift, move, or transport equipment and/or furniture weighing up to 20 pounds across campus to various classrooms and events. 
  • Able to work in outdoor weather conditions.

Interested candidates should email a cover letter with their resume to No phone calls, please. Click Here to download this information.


Employment is conditional upon the successful completion of a criminal background investigation. 

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Substitute School Teacher

  • We are currently interviewing for substitute teacher openings for K through 12th grades. Interested candidates should email  No phone calls, please.
  • Education
  • Bachelor’s degree is preferred but will consider candidates with some post-secondary education.
  • Experience
  • Previous teaching experience or substitute teaching experience is a plus.
  • Special Requirements
  • Employment is conditional upon the successful completion of a criminal background investigation. 

The Winston School San Antonio does not currently have any other open positions. 

All educational programs, services, activities, and employment of The Winston School San Antonio are available without regard to race, color, gender, religion, national or ethnic origin, age, genetics, or citizenship.

Employees of The Winston School San Antonio are protected under the Americans with Disabilities Act (ADA) of 1990 which prohibits discrimination and ensures equal opportunities for persons with disabilities in employment, state and local government services, public accommodations, commercial facilities, and transportation. Winston has made every effort to comply with the ADA. Individuals wishing to suggest additional modifications to facilitate the mobility of any member of the Winston community should contact a school administrator.