Help Desk Support Specialist I

Connect with the Greatest Generation and join us at St. Paul's! You will be able to make a difference in the lives of countless seniors by providing comfort and life-changing experiences every single day. Our team is looking for compassionate, caring and considerate companions to become angels for San Diego's residents and participants in the best years of their lives!

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

J ob 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.

St. Paul’s Benefits:

• Health, dental, vision, life
• Same day pay available!
• Flexible Vacation Time - 17 days!
• Paid Sick Time
• Education reimbursement - up to $3,000 a year!
• Qualified Public Student Loan Forgiveness (PSLF) employer
• 403(b) with match
• Child care available
• Employee referral bonuses
• Upward mobility!

You Make Us Who We Are!

At St. Paul’s Senior Services, we believe a diverse workforce has driven our history of enriching the lives of senior communities in San Diego, which is why we are committed to cultivating an environment where you feel empowered, supported and respected. By valuing your unique perspective, voice, strengths, experience and background, we aim to foster a culture where you feel included and comfortable being your true self. You matter!

St. Paul's is the leading provider of caring senior services since 1960. We have locations throughout San Diego County including 5 in San Diego (Bankers Hill), 2 in Chula Vista, and 1 in El Cajon. St. Paul's strives to be the most outstanding and innovative senior home and service provider in California. We are dedicated to serving the physical, spiritual and social needs of the elderly and community, fostering a culture of diversity and inclusion within the highest quality facilities, health care and programs consistent with affordable costs.

YOU MUST BE ABLE TO CLEAR FINGERPRINTS THROUGH DOJ AND FBI IN ADDITION TO A DRUG SCREEN CLEARANCE.

To learn more about St. Paul’s Senior Services, please visit

St. Paul’s Senior Services is an Equal Opportunity Employer