Tier 2 IT Helpdesk Technician

The Tier 2 IT Helpdesk Technician will provide on site escalated support and end user assistance in a Windows and macOS environment from our Philadelphia, PA location. The role emphasizes thorough troubleshooting, proactive documentation, and collaboration with IT teams on ongoing projects.

Responsibilities

• Take ownership of escalated Tier 1 tickets that require deeper investigation, including software conflicts, connectivity issues, and account or permission problems
• Deliver hands on and remote support for hardware, software, printers, mobile devices, and peripherals across Windows and macOS
• Create, modify, and disable user accounts in Active Directory and Microsoft 365, including mailbox and distribution list management and licensing
• Diagnose basic LAN, Wi Fi, VPN access, and other networking issues; escalate complex network faults as needed
• Image, configure, and deploy laptops and desktops; manage devices via Intune or comparable MDM solutions
• Troubleshoot Microsoft 365 apps such as Outlook, Teams, SharePoint, and OneDrive for end users
• Document all work thoroughly, update knowledge base articles, and contribute to standard operating procedures
• Escalate to Tier 3 with clear, detailed handoff notes to accelerate resolution
• Support IT initiatives including hardware refreshes, software rollouts, and office moves

Requirements

• 2 to 4 years of experience in IT support or helpdesk roles
• Solid troubleshooting skills across Windows 10 and Windows 11 environments
• Working knowledge of Active Directory including user and group management, password resets, and OU structure
• Hands on experience with Microsoft 365 apps such as Outlook, Teams, SharePoint, and OneDrive
• Familiarity with remote support tools such as ScreenConnect, TeamViewer, ConnectWise, or Splashtop
• Understanding of basic networking concepts including IP addressing, DNS, DHCP, VPN, and VLANs
• Experience with ticketing systems such as ConnectWise, ServiceNow, Jira, Freshservice, Zendesk, or similar
• Strong communication skills and the ability to explain technical issues clearly to non technical users

Technologies

• Windows 10/11
• Active Directory
• Microsoft 365
• ScreenConnect
• TeamViewer
• ConnectWise
• Splashtop
• Intune
• macOS
• Azure AD / Entra ID
• PowerShell
• Jira
• ServiceNow
• Freshservice
• Zendesk

Preferred Qualifications

• Experience with Intune or another MDM/endpoint management platform
• Familiarity with macOS support
• Exposure to Azure AD Entra ID and hybrid identity environments
• Basic PowerShell knowledge for administrative tasks
• Experience supporting a multi site or remote workforce

Certifications

• CompTIA A+
• CompTIA Network+
• Microsoft 365 Certified: Fundamentals (MS-900)
• ITIL Foundation
• HDI Support Center Analyst

Who You Are

• Patient and people oriented, understanding the stress of tech issues for users
• Methodical with a structured approach to troubleshooting and verification of resolution
• Dependable and trustworthy in supporting teammates and users
• Eager to learn and adapt to evolving technology and processes
• Clear communicator capable of detailed ticket notes and calm user guidance

Compensation

Salary range: USD 55,000–65,000 per year, depending on experience.

What We Offer

• Health, dental, and vision insurance
• 401(k) with company matching
• PTO and paid holidays
• Certification reimbursement and professional development support
• Collaborative and supportive team environment
• Clear path to progression to Tier 3 or Systems Administrator roles
• Parental leave
• Life insurance

Work Location

Onsite in Philadelphia, PA