Building and Grounds Supervisor

Position Overview

Trinity-Pawling School seeks an experienced, hands-on Buildings and Grounds Supervisor with strong trade and technical expertise to lead the daily operation, maintenance, and improvement of the School’s campus facilities and infrastructure.

This role oversees a 247-acre campus comprising 8 student residential buildings, 49 faculty residences, athletic fields, an ice hockey rink, an athletic center, a dining hall, a health center, an arts center, a classroom building, tennis courts, and a vehicle fleet.

Ideal candidates will be highly skilled engineers or trades professionals (e.g., master electrician, HVAC specialist, plumber, or construction professional) who thrive in a hands-on leadership role. The Supervisor will manage the facilities team day-to-day while remaining actively engaged in troubleshooting, repairs, system optimization, and campus improvement projects.

This position serves as the primary first responder to time-sensitive campus issues on a 24/7 basis, with support from the Director of Facilities or another Facilities team member to ensure coverage every day of the year. The Supervisor also works closely with the Director of Building Services and Associate Director of Facilities.

Key Responsibilities

Hands On Leadership

• Serve as the lead technical expert for campus building systems, including HVAC, electrical, plumbing, mechanical, and life-safety systems.
• Diagnose and resolve complex system issues efficiently.
• Perform or oversee advanced repairs and installations as needed.
• Maintain and continuously improve preventive maintenance programs.

Supervision & Team Management (8-10 Direct Reports)

• Lead, schedule, and supervise maintenance, ice rink, and grounds staff.
• Train team members in safety protocols and technical best practices.
• Create and manage clear work-order procedures, ensuring timely completion.
• Foster a strong service-oriented culture that supports students, faculty, and staff who live on or commute to campus.

Campus Infrastructure & Facilities

• Oversee and perform maintenance across facilities ranging from early 1900s construction to modern buildings, including academic, administrative, residential, faculty, and athletic facilities.
• Monitor building systems and equipment conditions proactively, addressing concerns before they become critical.
• Ensure timely completion of deferred maintenance projects to avoid long-term disruptions.
• Maintain campus appearance to reflect the School’s high standards.
• Manage required inspections of building systems on schedule.
• Maintain the vehicle fleet, ensuring all equipment and transportation resources are clean, safe, and pass regular inspections.
• Manage resources that support routine daily operations, including trash and recycling removal, mail pickup and drop-off, and receipt of large deliveries.

Grounds & Snow Removal

• Oversee grounds maintenance, including tree care, pond care, and native landscaping.
• Ensure lawns are regularly trimmed, walkways are clear of debris and hazards, and all outdoor spaces are safe and well-maintained.
• Manage all aspects of snow and ice removal across a 24/7 boarding campus, coordinating staffing and resources to respond promptly to weather events.

Events & Student Activities

• Provide setup, teardown, and logistical support for on-campus events, including student activities, leadership meetings, and major School events such as Opening of School and Graduation.
• Collaborate with faculty, staff, and external vendors to ensure smooth event operations.
• Assist with emergency response and facilities-related issues as needed.

Projects & Capital Improvements

• Participate in renovation and capital improvement projects.
• Review plans and specifications for constructability and system compatibility.
• Develop and maintain working knowledge of local contractors and vendors.
• Assist in long-term infrastructure planning and energy efficiency initiatives.

Safety & Compliance

• Foster a culture of safety and ensure all work complies with applicable federal, state, and local regulations, codes, and laws.
• Maintain fire, security, and life-safety systems.
• Serve as a key member of the School’s emergency response team.
• Oversee emergency maintenance procedures in coordination with School leadership.

Budget & Resource Management

• Support the Director of Facilities in developing and maintaining the departmental operating budget.
• Source materials and manage maintenance inventory.
• Assist in evaluating and selecting outside service providers as needed.

Required Qualifications

• 7+ years of progressive experience in facilities maintenance, construction, or a skilled trade.
• Must reside within 10 miles of the School’s campus and hold a valid driver’s license.
• Demonstrated ability to troubleshoot complex building systems.
• Experience leading, mentoring, and supervising a facilities team.
• Proven success managing preventive maintenance programs and work-order systems.
• Ability to read blueprints and technical schematics and interpret building codes.
• Strong relationship-building skills with vendors, contractors, and across the broader School community.
• Customer service-oriented mindset — understands that responsiveness and approachability are as important as technical expertise.

Preferred Qualifications

• Formal training, licensure, or certification in a skilled trade (e.g., electrical, HVAC, plumbing, or mechanical systems).
• Knowledge of federal safety, fire, and accessibility regulations, and New York State and Village of Pawling building codes.
• Experience in a school, college, boarding school, or comparable campus environment.
• Experience in maintaining older or historic buildings.
• Experience starting up, shutting down, and maintaining an ice rink.
• Familiarity with energy management or building automation systems.
• Heavy equipment operation experience (e.g., lawn care equipment, excavator, forklift, snow removal equipment).

Personal Attributes

• Hands-on leader who leads by example.
• Strong problem-solver with solid mechanical aptitude.
• Calm, decisive, and responsive under pressure or during emergencies.
• Service-minded, reliable, and collaborative.
• High integrity with an unwavering commitment to safety.

Physical Requirements

• Ability to lift 50+ pounds.
• Ability to work indoors and outdoors in all weather conditions.
• Ability to access roofs, crawl spaces, and mechanical rooms.
• Availability outside normal working hours for events and emergencies, including evenings and weekends.

The salary range for this position is $80,000 - $95,000 per year. This range represents our good faith estimate for this position. We consider additional factors such as education, experience, skills, as well as the needs of the School at the time of the offer. All job offers are contingent upon the candidate’s successful completion of a background & fingerprint check, reference checks, and pre-employment screening, as applicable

Pay: $80,000.00 - $95,000.00 per year

Benefits:

• Dental insurance
• Health insurance
• Health savings account
• Life insurance
• Paid time off
• Retirement plan
• Vision insurance

Application Question(s):

• Are you located within 10 miles of Trinity-Pawling's campus?

Location:

• Pawling, NY 12564 (Preferred)

Work Location: In person