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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.

Director of Buildings & Grounds (2023-2024)

Job Title: Director of Buildings & Grounds
Classification: Non-Faculty
FLSA Status: Exempt
Supervisor: Head of School
Supervises: Maintenance Technicians and Facilities Personnel


  • Oversee all aspects of all facilities including repairs, maintenance, modernization, expansion, technology, and school-level issues related to building security and the security monitoring system
  • Organize, administer, and lead a comprehensive program of maintenance and custodial services that provides and maintains the facilities, grounds, equipment, and furnishings of the school
  • Develop and implement a multi-year comprehensive maintenance program that is both corrective and preventative for the upkeep of all facilities, grounds, and the major facilities systems (HVAC, mechanical, plumbing, electrical and structural)
  • Provide an efficient work order system for repairs of facilities and equipment that ensures all maintenance and repairs are completed in a timely fashion
  • Schedule and monitor monthly fire drills in coordination with the Head of School and School Personnel
  • Collaborate with the Head of School on the execution of a 10-year Capital Development/Improvement Facilities Plan
  • Serve as a member of the Crisis Team
  • Contact the Head of School to report on road conditions and accessibility of buildings and grounds during severe weather conditions
  • Supervise the grounds to ensure that safe conditions exist
  • Provide regular work order status to the Head of School and recommend facility improvement and modernization to improve the systems, equipment, and facilities
  • Ensure that facilities maintenance staff are present at all school events
  • Establish and implement an effective summer and non-school-day program of specialized cleaning and repairs
  • Promptly report to the Head of School any emergency and/or any unsafe or unhealthy conditions of facilities, equipment, systems, or grounds with recommendations for improvement or correction
  • Develop a custodial services plan that outlines the tasks and expectations for custodial employees, indicating a detailed daily and periodic schedule for cleaning and repairs
  • Establish and implement, in accordance with OSHA regulations, a program of safety, accident prevention, and health maintenance for all employees, including safe and proper use of equipment, vehicles and materials, identification and prevention of hazards, air quality controls, and Right-To-Know programs
  • Conduct regular inspections of all school facilities, grounds, and equipment to ensure that high standards of cleanliness, attractiveness, and safety are maintained
  • Develop and recommend a Building and Grounds budget; and administer the approved budget
  • Maintain current drawings and engineering records describing facilities, equipment, and grounds
  • Maintain a fixed assets inventory
  • Maintain an inventory control system and purchase supplies, parts, and equipment through the established bid or price quote process
  • Approve the specifications and recommend contractors to perform maintenance and repair services and supervise and inspect the work performed
  • Develop, implement, and monitor an energy conservation program, making recommendations for efficiency and reduction in costs of operating the facilities
  • Provide and maintain an efficient and effective waste disposal system
  • Establish vendor relationships and conduct contract negotiations and as warranted construction management


  • 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 or equivalent experience and/or certifications in a related field
  • At least five years of experience in construction and/or property management, with a minimum of three years in a supervisory capacity
  • Demonstrated knowledge of building/construction codes, health and safety regulations, financial and management practices, purchasing, supervision of personnel; maintaining city/state regulations regarding the maintenance of buildings and equipment
  • Hold and maintain a valid driver’s license for the type of equipment to be driven, with no serious violations,
  • Good written and oral communication skills
  • Able to work effectively as a member of an interdisciplinary team
  • Exposure to chemical substances used for cleaning and operation of equipment
  • Able to sit in a stationary position, move throughout the campus, operate a computer, ascend and 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 outdoors in a variety of extreme weather conditions

Additional Information:

  • Employment is conditional upon the successful completion of a background check
  • Salary is competitive based on experience and background
  • Interested candidates should email and  No phone calls, please.

Please click here to download this description in PDF Format

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.