System Administrator and Help Desk Lead

The Hill School Mission: The Hill School prepares young people from across the country and around the world for college, careers, and life. Within a family school environment and a rigorous liberal arts curriculum, we challenge our young people to work hard; think and reason; seek fulfillment; serve the common good; and be prepared to lead as citizens of the world, uniquely guided by our motto, "Whatsoever Things Are True."

Position Summary

The System Administrator and Help Desk Lead is a key member of the Information Technology Services team, responsible for maintaining critical IT systems while leading day-to-day technical support operations. This role supports a wide range of technology needs for faculty, staff, and institutional systems, managing complex tickets, guiding Level 1 technicians, and administering core infrastructure tools. The ideal candidate combines deep technical expertise with strong leadership and user-facing communication skills.

Responsibilities

• Serve as the primary escalation point for complex or unresolved Level 1 support tickets.
• Provide comprehensive help desk support for hardware, software, network, and user-facing systems.
• Troubleshoot and resolve software issues, including installations, configurations, and performance problems.
• Support hardware devices, including desktops, laptops, printers, scanners, and peripheral equipment.
• Deliver technical support for mobile devices (iOS/Android), A/V systems, and game/special-use systems.
• Respond to all help desk tickets with urgency and professionalism, ensuring timely resolution.
• Instruct users on how to use common applications such as Microsoft Office, Zoom, and institutional tools.
• Rapidly learn and support new software systems used by faculty and staff.
• Manage and maintain Intune, Jamf, Connectwise suite, Medicat (EMR).
• Diagnose and resolve hardware-level network issues and connectivity problems.
• Mentor and guide Level 1 Help Desk staff, providing technical oversight and daily support leadership.
• Create and update IT knowledge base articles, documentation, and support resources.
• Support IT leadership in developing, implementing, and refining technology policies and workflows.
• Promote and implement basic cybersecurity best practices, including user awareness, software patching, and endpoint protection monitoring.
  
  

Qualifications

• Bachelor's in Computer Information Systems or Computer Science (4-year program)
• Candidates with a certification in systems administration or cyber security are preferred. Additionally, Microsoft, VMware, or Aruba certifications are considered a plus.
• Two years' experience in system and network administration.
• Knowledgeable in IT best practices, including ITIL and Microsoft Operations Framework (MOF).
  
  

ATTITUDE AND DEMEANOR

• Publicly support the mission and vision of The Hill School in a positive and professional manner.
• Work as a dynamic team member in a professional collaborative environment.
• Energetic and organized enough to thrive in an extremely fast-paced environment while collaborating with a growing team to produce great work.
• Ability to wear many hats, learn new things every day, and have the ability to switch from a variety of roles with ease and excitement.
• Communicate effectively with warmth, sensitivity, humor, and understanding as they deal with administrative colleagues, teachers, students, alumni, parents, faculty, staff, and program associates.
• Possess a "service attitude" - willingness to be flexible to meet the needs of the department and school.
  
  

Position is contingent upon successful completion of certain background checks, including criminal history background checks, fingerprint-based background checks, reference checks, employment history checks, and educational background checks, upon hire and during the course of your employment, to the extent permitted by law and consistent with the School's policies regarding employment eligibility.