Tier 2 IT Support Specialist

The 20•Annapolis, MD

6d•$65,000 - $80,000•Hybrid

About The Position

This position is being recruited by The 20 on behalf of EnglerIT. For more than 20 years, EnglerIT has delivered tailored IT solutions that help organizations stay secure, efficient, and confidently operational. Their mission is simple: provide reliable, cost-effective technology that removes complexity and supports long-term business growth. EnglerIT is a results-driven IT Managed Services Provider (MSP) serving organizations across Maryland, Washington DC, and Northern Virginia. Known for their people-first approach, they combine deep technical expertise with clear communication and practical outcomes across managed IT, cybersecurity, cloud services, Microsoft 365, networking, VoIP, and more. The ideal candidate is highly technical, communicates clearly with end users, and thrives in a fast-paced, customer-centric environment. You will serve as a trusted resource for diagnosing issues, implementing solutions, and ensuring systems remain stable, secure, and efficient.

Requirements

3+ years of IT support, technical support, or systems administration experience.
Strong knowledge of Windows OS, Windows Server, Active Directory, Azure AD, Microsoft 365, and networking fundamentals.
Experience repairing and supporting desktop and laptop hardware.
Strong communication skills and experience working in a multi-client or MSP environment.
Valid drivers license and ability to travel regionally.

Nice To Haves

Certifications (CompTIA A+, Network+, Security+, Microsoft, or equivalent experience).
Virtualization experience (VMware, Hyper-V).
PowerShell or automation exposure.
Experience with RMM/PSA and documentation platforms.
Exposure to macOS, mobile platforms, or Google Workspace.

Responsibilities

Provide Tier 2 onsite and remote technical support for end users, workstations, servers, and client environments.
Troubleshoot hardware, software, operating systems, VPNs, security tools, and business applications.
Administer and support Windows Server, Active Directory, Azure AD, Group Policy, DNS/DHCP, and Microsoft 365.
Perform system upgrades, patching, imaging, software deployments, and hardware repairs.
Support network infrastructure including firewalls, switching, wireless, VPNs, and physical cabling.
Deliver desktop support across Windows and macOS, with exposure to iOS and Android.
Document work using ITSM/RMM tools (e.g., Kaseya BMS/VSA, IT Glue).
Travel to client sites as needed and collaborate with internal teams to ensure service continuity.