Help Desk Level 2 Technician

The Level 2 Help Desk Technician provides technical support to faculty, staff, students, and parents and serves as an escalation point for technical issues that require more advanced troubleshooting. The position supports the school's computers, mobile devices, classroom technology, Microsoft 365 environment, network connectivity, printers, audiovisual systems, and other technology resources.

The Level 2 Help Desk Technician works closely with other members of the Information Technology Services (ITS) Department to ensure that technology is reliable, accessible, and effectively supports teaching, learning, and school operations. This position requires strong technical troubleshooting skills as well as excellent communication, patience, and customer service.

Help Desk and User Support

• Provide Level 2 technical support to faculty, staff, students, and parents.

• Serve as an escalation point for technical issues that cannot be resolved through initial Help Desk support.

• Diagnose and resolve hardware, software, operating system, account, network connectivity, printing, and application issues.

• Respond to support requests submitted through the school's Help Desk/ticketing system, telephone, email, Teams, and in-person requests.

• Prioritize support requests based on urgency, instructional impact, and operational needs.

• Maintain accurate records of support requests, troubleshooting steps, equipment changes, and resolutions.

• Follow problems through resolution and communicate status and next steps to users.

• Escalate issues to network, systems, security, application, or vendor support personnel when appropriate.

• Assist other Help Desk technicians with troubleshooting and provide technical guidance as needed.

Computers and Mobile Devices

• Configure, deploy, maintain, troubleshoot, and repair school-owned computers and mobile devices.

• Support both macOS and Windows computers in a mixed-platform environment.

• Support iPads, iPhones, and other mobile devices as required.

• Install and configure operating systems, applications, printers, peripherals, and updates.

• Assist with computer imaging, provisioning, enrollment, and automated deployment.

• Diagnose hardware problems and coordinate warranty or vendor repairs when necessary.

• Prepare replacement and loaner equipment for faculty, staff, and students.

• Assist with annual and summer device collection, maintenance, inventory, deployment, and replacement projects.

Microsoft 365 and Collaboration Services

• Provide technical support for Microsoft 365 applications and services, including:

• Microsoft Teams

• Outlook and Exchange Online

• OneDrive

• SharePoint

• Word

• Excel

• PowerPoint

• Troubleshoot Teams meetings, chats, channels, permissions, shared files, and collaboration issues.

• Assist users with OneDrive synchronization, file sharing, permissions, and file recovery.

• Troubleshoot SharePoint and Teams document libraries and access issues.

• Assist users with Outlook configuration, calendars, shared mailboxes, and related email issues.

• Help faculty and staff effectively use Microsoft 365 tools for instruction, collaboration, and administrative work.

Networking and Connectivity

• Troubleshoot wired and wireless network connectivity problems.

• Assist users with connecting school-owned and approved personal devices to appropriate networks.

• Identify potential network infrastructure problems and escalate them to appropriate technical staff.

• Assist with basic testing and troubleshooting of network equipment and cabling as needed.

Printing and Peripheral Support

• Install, configure, and troubleshoot printers and multifunction devices.

• Diagnose printing, scanning, driver, queue, and connectivity problems.

• Support keyboards, mice, docking stations, monitors, adapters, external storage devices, and other peripherals.

• Coordinate service and repair with vendors when necessary.

Audiovisual and Event Support

• Support video conferencing using Microsoft Teams and other approved platforms.

• Configure and troubleshoot cameras, microphones, speakers, displays, projectors, and presentation equipment.

• Provide technical assistance for faculty meetings, parent programs, assemblies, presentations, and special events as required.

• Assist with setup, testing, operation, and breakdown of audiovisual equipment.

Security

• Follow school policies and established information security practices.

• Assist users with multifactor authentication and account security procedures.

• Respond appropriately to suspected phishing messages, compromised accounts, malware, and other security concerns.

• Escalate suspected cybersecurity incidents according to established procedures.

• Assist users with safe computing practices and protection of school and student information.

• Maintain appropriate confidentiality when working with student, faculty, staff, and parents information.

Technology Projects

• Participate in school-wide technology initiatives, upgrades, migrations, and deployments.

• Assist with testing and implementation of new hardware, software, and cloud services.

• Participate in summer technology projects, including classroom technology upgrades, device deployment, computer replacement, software installation, and inventory.

• Work collaboratively with Technology Department staff and other departments on projects affecting school operations.

• Perform other technology-related duties as assigned.

Required Qualifications

• Two or more years of experience providing technical support in a Help Desk, desktop support, or similar environment.

• Demonstrated experience of troubleshooting computers, applications, peripherals, and user accounts.

• Experience supporting macOS and/or Windows operating systems.

• Experience supporting Microsoft 365 applications and services.

• Working knowledge of Microsoft Entra ID, Active Directory, or similar identity-management systems.

• Understanding basic networking concepts, including TCP/IP, DHCP, DNS, Wi-Fi, and VPN technologies.

• Experience installing and troubleshooting printers, displays, projectors, and computer peripherals.

• Strong analytical and troubleshooting skills.

• Strong written and verbal communication skills.

• Excellent customer service and interpersonal skills.

• Ability to communicate technical information clearly to users with varying levels of technical experience.

• Ability to manage multiple priorities and work effectively in a busy school environment.

• Ability to work independently while collaborating effectively as part of a Technology Department team.

Preferred Qualifications

• Previous technical-support experience in a K-12 school, college, university, or other educational environment.

• Experience supporting both Apple and Windows devices.

• Experience with Microsoft Teams, OneDrive, SharePoint, Outlook, and Microsoft 365 administration.

• Experience with Apple device management and deployment.

• Experience with Microsoft Intune or another mobile device/endpoint management platform, such as JAMF, and Apple School Manager.

• Familiarity with student information systems, learning management systems, and other educational technology platforms.

• Experience supporting classroom audiovisual and presentation systems.

• Experience with automated computer deployment and software distribution.

• Familiarity with cybersecurity practices applicable to educational environments.

• Relevant technical certifications such as CompTIA A+, Network+, Microsoft, Apple, or equivalent professional certifications.

Knowledge, Skills, and Abilities

The successful candidate will demonstrate:

• Strong technical troubleshooting and problem-solving skills.

• A methodical approach to diagnosing complex technical problems.

• A strong commitment to customer service.

• Patience and professionalism when assisting students and adults with varying levels of technical proficiency.

• The ability to explain technical concepts in clear, understandable language.

• Good organizational and time management skills.

• Attention to detail and accurate documentation.

• The ability to prioritize issues based on their impact on teaching, learning, and school operations.

• The ability to work effectively both independently and collaboratively.

• Sound judgment regarding when an issue should be escalated.

• Respect for confidentiality and the privacy of student, faculty, and staff information.

• Flexibility and the ability to adapt to changing technology and school priorities.

Physical and Scheduling Requirements

The position requires regular movement throughout classrooms, offices, meeting spaces, and other areas of the school campus. Duties may include lifting, carrying, installing, and relocating computers, monitors, printers, audiovisual equipment, and other technology.

The position may occasionally require work outside normal school hours to support maintenance, upgrades, deployments, special events, or emergency technical issues. Summer periods may include significant equipment deployment, classroom technology maintenance, inventory, and system-upgrade projects.

Success in This Position

A successful Level 2 Help Desk Technician combines strong technical skills with a service-oriented approach to supporting a school community. The technician takes ownership of technical problems, communicates effectively with users, documents work thoroughly, and works collaboratively with colleagues to resolve issues.

Success is measured not only by resolving technical problems, but also by minimizing disruptions to teaching and learning, providing users with a positive support experience, and contributing to a reliable, secure, and effective technology environment for the school community.

Working at Choate: Choate Rosemary Hall is a coeducational, independent secondary school located in central Connecticut with 865 boarding and day students and over 400 employees. Choate serves intellectually gifted and motivated students of diverse backgrounds from across the globe whose commitment to serious study is enhanced in an academically challenging and personally supportive setting.

Choate provides students with transformative and meaningful experiences that instill lifelong habits of learning, leadership, and service, shaped by innovative and passionate educators. Teaching faculty at Choate are innovative, collaborative, and committed to our students' intellectual, social, emotional, and character development. Our faculty understands that each of our students has the potential for growth and works to encourage students to develop their own ideas and voices in learner-centered environments.

For its students and employees alike, Choate strives to be a diverse and inclusive community where all feel valued and embraced. On our campus, principled individuals from diverse backgrounds are united through common purpose, active engagement, and mutual respect. We celebrate differences and the richness of our varied backgrounds and experiences. Recognizing that working in an inclusive community can also present challenges, we embrace those challenges through ongoing dialogue and interaction, enhancing empathy and appreciation for those whose perspectives differ from our own.

Choate prohibits in all its programs, including hiring and employment practices, discrimination against or harassment of any member or group based upon age, gender, race, color, national origin, ancestry, religion, marital status, sexual orientation, disability, genetic information, gender identity or expression, veteran status, or any other category protected by Connecticut or federal law, except in the case of a bona fide occupational qualification.