Systems Administrator

Job Level
Mid-level position
Job Category
  • Technology
  • Systems / Operations
Job Status
Areas of Responsibility
  • Systems / Operations
  • Systems

About Dexter Southfield

Dexter Southfield is an independent school where boys and girls in Pre-K through Class 12 develop their individual talents and build an ethical foundation for life. Through a classical education and innovative programming, students learn to lead with confidence and serve with compassion. Our 36-acre campus is located on the Brookline-Boston line, just minutes from the city’s best museums, libraries, hospitals, performing arts venues, colleges, and universities—all of which serve as an extension of our classrooms. At Dexter Southfield, we approach everything we do with enthusiasm and commitment, living by our School’s motto: “Our Best Today, Better Tomorrow.”

About You 

You are a highly productive self-starter with excellent analytical, strategic, relationship-building, and organizational skills. You are flexible and resilient, able to adapt to an ever-changing landscape, and identify what it takes to get the job done. Strong communication skills with an impeccable attention to detail are your trademark. You have a proven yourself as someone who can take on increased responsibility and tackle competing priorities with integrity, humor, and sound judgment.   

The Position
This position supports the overall information technology efforts of the school and works closely with the Director of Information Technology and other members of the school community, including faculty, staff, students, and parents. To be successful in this role, you must be able to:

  • Triage requests for technology assistance related to hardware, software, networking, etc.
  • Properly configure and update systems and establish user accounts
  • Ensure and track proper operation of printers and printer servers
  • Install and secure operation of security tools on School-owned devices
  • Work with Director of Information Technology to establish and deliver high level of service
  • Provide operational and end-to-end training and support for school- and student-owned devices
  • Manage end-user inventories (e.g., desktops, laptops, Surfaces, toner, etc.)
  • Support installed AV and Touch view systems in classrooms and shared spaces
  • Create, change, deactivate, and license user accounts on systems managed by IT
  • Provide Top level support on server and network issues.
  • Ensure proper security updates and operation of virtual and physical server environment
  • Support DNS, DHCP, and WINS/NETBUI protocols
  • Support MS Azure/AD and Office 365 integration
  • Manage VMware Server Virtual environment
  • Manage Mitel VIOP phone systems
  • Manage MS o365 administrator console.
  • Support online software for students and Faculty.
  • Managed INTUNE security compliance tools
  • Works with Director of Information Technology to properly configure and operate servers
  • Other duties and projects as assigned to support the operations of the School.



  • Bachelor’s degree in computer science, information technology, or related field
  • At least 5 years’ full-time employment experience (or equivalent) in the following areas:
    • MS Windows 10 & 11 OS
    • MS Server 2016/2019 OS
    • MS Azure cloud solution
    • VMware vSphere
    • Mitel / Micollab phone system
  • Ability to read, analyze, and interpret relevant periodicals and professional journals
  • Strong communication and language processing skills (oral, written, listening, and analysis), with an ability to independently read and clearly write reports and business correspondence
  • Excellent attention to detail  
  • Strong interpersonal and relationship-building skills with an ability to effectively present information and respond to questions from diverse constituencies
  • Demonstrated understanding of mathematical concepts and an ability to effectively apply them in workplace situations (e.g., probability and statistical inference)
  • Knowledge of effective leadership principles (e.g., setting a vision, planning, implementation, and outcome assessment)
  • Ability to independently think logically to effectively problem-solve complex issues
  • A good sense of humor and ability to effectively work independently and as part of a team.

This is a full-time, 12-month position. This job requires use of extremities and the ability to lift, carry, push, and/or pull materials and equipment weighing up to 50 pounds. Work assignments are typically performed under minimal temperature variations in a generally hazard-free environment. The role will require occasional extended hours that includes after school, evenings, and weekends during special events or peak work periods.

All employees are required to verify employment eligibility and successfully complete CORI, SORI, and fingerprint-based background checks as a condition of employment.

At Dexter Southfield, we promote a culture of excellence that extends beyond academics, athletics, and the arts. We offer a culture in which employees feel valued and respected and are rewarded with a generous employee benefit package.  

How to Apply

Qualified candidates are encouraged to visit the Careers page of our website to submit a cover letter and resume through our online application portal at