Help Desk Support Specialist I

St. Paul's Senior Services; San Diego (CA); On-site; USD 48,000 - 64,000; Full time

Job summary

St. Paul’s Senior Services in San Diego, CA seeks a full-time onsite IT Support specialist to maintain and support end-user technology across on-premises and cloud environments—including Windows PCs, Macs, and Microsoft 365 services. The role covers device deployment, remote support, and security triage.

You will manage end-user identities (Entra ID), perform basic administration, and create knowledge-base articles to streamline support. Strong teamwork across IT is required.

Qualifications

• Experience in Windows and macOS troubleshooting with Microsoft 365 and Entra ID.

Responsibilities

• Deploy and troubleshoot Windows PCs and Macs.
• Provide remote management and support for enterprise endpoints.
• Asset tagging and installation of new desktops and peripherals.
• Create and deploy standard workstation images; familiarity with Autopilot is a plus.
• Assist in network diagrams and cable installation.
• Monitor deployed technologies and report recurring issues.
• Support Microsoft 365 apps (Outlook, Teams, OneDrive, SharePoint).
• Perform basic Microsoft 365 and Entra ID administration and troubleshooting.
• Provide initial security triage for phishing and BEC incidents.
• Document fixes and updates in a knowledge base.

Skills

Windows

macOS

Microsoft 365

Entra ID

PowerShell

Remote support

Documentation

Education

Associate degree (A.A.) or equivalent

Tools

Active Directory

Group Policy

Windows Registry

WMI

Microsoft Intune

PowerShell scripting

Job description

This is a Full-time onsite position located in San Diego, CA.

Job Summary

Provides Level 1 technical support independently and as a member of a cross-functional IT team. Supports and maintains enterprise end-user technology across on-premises and cloud environments, including endpoint hardware, operating systems, Microsoft 365 services, identity and access, mobile devices, business applications, and remote/field users.

Essential Duties and Responsibilities:

• Perform hardware and software deployment, upgrades, troubleshooting, repairs, and maintenance for Windows PCs, Apple Mac computers, laptops, monitors, printers, and other supported peripherals.
• Provide remote management and support for enterprise endpoints, including remote assistance, patching, software distribution, device inventory, and basic compliance or management-status checks.
• Asset tag, label, configure and install all new desktop computers including personal computers, Macs, laptops, monitors, and printers.
• Create, maintain, and deploy standard workstation images and software packages when required; familiarity with Windows Autopilot and modern provisioning workflows is a plus.
• Assist in creation of network diagrams and installation of cable runs.
• Monitor the effectiveness of deployed technologies, gather end-user feedback, identify recurring issues, and recommend improvements or escalation when appropriate.
• Provide support for business and production applications as well as Microsoft 365 applications and services, including Outlook, Teams, OneDrive, SharePoint, and standard productivity applications.
• Perform basic Microsoft 365 and Microsoft Entra ID administration and troubleshooting, including user account status, password and lockout issues, MFA, Conditional Access-related sign-in issues, and basic review of authentication/sign-in logs before escalation.
• Provide initial security triage by recognizing potential phishing, Business Email Compromise (BEC), suspicious Outlook forwarding or inbox rules, and endpoint security alerts.
• Use approved PowerShell commands and remediation scripts for basic troubleshooting and support tasks, including authentication, synchronization, device, and connectivity issues.Document resolved issues, troubleshooting procedures, and repeatable fixes in clear knowledge base articles so solutions can be reused by the support team and incorporated into future AI-assisted support and knowledge platforms.

Minimum Qualifications:

• Familiar with troubleshooting and configuration in Windows and macOS environments, with working knowledge of Microsoft 365, Microsoft Entra ID, endpoint management, and support for mobile devices.
• Person should have the ability to lift heavy computer equipment such as computers, and printers, sometimes weighing up to about 90lbs.
• Microsoft or other relevant IT support, Microsoft 365, endpoint management, or security certifications are highly desired.
• Familiarity with Active Directory, Group Policy, Windows Registry, Windows Management Instrumentation (WMI), and basic PowerShell or approved scripting tools; familiarity with Microsoft Intune and Microsoft Entra ID is highly desired.
• Ability to troubleshoot common Microsoft 365 sign-in, MFA, Outlook, Teams, OneDrive, SharePoint, Intune, and remote-endpoint issues; recognize common security concerns; follow documented escalation procedures; and create clear, reusable technical documentation.

Education And/or Experience:

• Education: Associate degree (A.A.) or equivalent from a two-year college or technical school, with 2 to 3 years of experience troubleshooting and repairing personal computers and printers, or an equivalent combination of education and experience.
• Experience: Minimum 12 months of experience troubleshooting cabling in a network environment and familiarity with tools such as cable testers, punch-down tools, cable crimpers, and cable toners. Experience supporting Microsoft 365, remote users, mobile devices, or managed endpoints is strongly preferred.