The Helpdesk Technician - Level 2 is responsible for resolving escalated technical issues that require deeper troubleshooting beyond Level 1 support. This position provides both remote and onsite support to end users, focusing on software, hardware, and network issues of moderate complexity. The role includes assisting with system configurations, permissions, user setups, and documentation to drive operational excellence across our IT systems.

Beyond technical expertise, this role requires a strong customer service mindset and a helpful, friendly attitude. The ideal candidate is approachable, patient, and dedicated to ensuring each interaction leaves the user feeling supported and confident. The Level 2 Technician will actively communicate with team members and end users to provide clear explanations, deliver timely solutions, and foster a positive, service-oriented IT culture across the organization.

Key Responsibilities

• Resolve complex user issues escalated from Level 1 Helpdesk staff, providing timely and professional support.
• Troubleshoot and maintain Windows 11 Pro and macOS operating systems, including application and hardware problems.
• Administer Active Directory for password resets, user and group management, and Group Policy (GPO) updates.
• Manage Microsoft 365 services, including Exchange Online (mailboxes, distribution lists), SharePoint, OneDrive, and Teams.
• Provide guidance on Multi-Factor Authentication (MFA), SSO, and endpoint security best practices.
• Troubleshoot network issues such as connectivity, printers, Wi-Fi, and VPN access.
• Support software installations, updates, and patch management processes.
• Document recurring technical issues, root causes, and recommended long-term fixes.
• Escalate unresolved or critical issues to Level 3 or Systems Administrators as appropriate.
• Mentor Level 1 Helpdesk staff, sharing technical expertise and best practices.
• Participate in IT improvement initiatives to enhance service delivery and system reliability.

Required Qualifications

• 5+ years of hands-on IT support experience in a multi-location environment.
• Strong knowledge of Windows and macOS operating systems.
• Proficient in Microsoft 365 administration (Exchange Online, Teams, SharePoint, OneDrive).
• Skilled in Active Directory management and Group Policy configuration.
• Familiarity with Azure services and Hyper-V virtualization.
• Understanding of networking concepts (IP addressing, DNS, DHCP, VPN).
• Experience implementing and managing SSO/MFA for user authentication.
• Working knowledge of Mobile Device Management (MDM) solutions for endpoint compliance.
• Excellent communication, problem-solving, and time management skills.
• Ability to manage multiple tickets while meeting SLA and documentation standards.

Nice to Have

• Experience in an ITIL-based helpdesk environment.
• Exposure to endpoint protection tools (Defender, Sophos, or CrowdStrike).
• Experience with asset management systems or IT inventory tracking.
• Familiarity with PowerShell scripting for automation and diagnostics.
• Bilingual (English/Spanish) a plus.

Salary Range: $47,000 - $68,000