Help Desk Support Specialist I

St. Paul's Senior Services•San Diego, CA

10d•$22 - $33•Onsite

About The Position

Provides Level 1 technical support independently and as part 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 and field users. This is a full-time, onsite position in San Diego, California. The role also involves documenting solutions for reuse by the support team and future AI-assisted support and knowledge platforms. Applicants must be able to clear DOJ and FBI fingerprint checks and a drug screen.

Requirements

Working familiarity with troubleshooting and configuration in Windows and macOS environments, Microsoft 365, Microsoft Entra ID, endpoint management, and mobile device support.
Ability to lift computer equipment, including computers and printers weighing up to approximately 90 pounds.
Familiarity with Active Directory, Group Policy, Windows Registry, Windows Management Instrumentation (WMI), and basic PowerShell or approved scripting tools.
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.
Associate degree (A.A.) or equivalent from a two-year college or technical school, and 2 to 3 years of experience troubleshooting and repairing personal computers and printers, or an equivalent combination of education and experience.
At least 12 months of experience troubleshooting cabling in a network environment and familiarity with cable testers, punch-down tools, cable crimpers, and cable toners.
Ability to clear DOJ and FBI fingerprint checks and a drug screen.

Nice To Haves

Microsoft or other relevant IT support, Microsoft 365, endpoint management, or security certifications.
Familiarity with Windows Autopilot and modern provisioning workflows.
Strongly preferred experience supporting Microsoft 365, remote users, mobile devices, or managed endpoints.
Highly desired familiarity with Microsoft Intune and Microsoft Entra ID.

Responsibilities

Deploy, upgrade, troubleshoot, repair, and maintain Windows PCs, Apple Mac computers, laptops, monitors, printers, and other supported peripherals.
Provide remote endpoint management and support, including remote assistance, patching, software distribution, device inventory, and basic compliance or management-status checks.
Asset tag, label, configure, and install new desktop computers, Macs, laptops, monitors, and printers.
Create, maintain, and deploy standard workstation images and software packages when required.
Assist with creating network diagrams and installing cable runs.
Monitor deployed technology, gather end-user feedback, identify recurring issues, and recommend improvements or escalation as appropriate.
Support business and production applications, Microsoft 365 applications and services, 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 authentication or sign-in log review before escalation.
Conduct initial security triage by recognizing potential phishing, Business Email Compromise, suspicious Outlook forwarding or inbox rules, and endpoint security alerts.
Use approved PowerShell commands and remediation scripts for basic authentication, synchronization, device, and connectivity troubleshooting and support tasks.
Document resolved issues, troubleshooting procedures, and repeatable fixes in clear knowledge base articles.