Help Desk Technician Tier 2

Benefits

• 401(k) matching
• Bonus based on performance
• Company car
• Competitive salary
• Dental insurance
• Free food & snacks
• Health insurance
• Opportunity for advancement
• Paid time off
• Training & development
• Vision insurance

Job Title: Help Desk Technician – Tier 2

Full time – In Office - Annapolis, MD

About us: ICSI is a leading Managed Service Provider (MSP) dedicated to delivering top-notch IT solutions to our clients. We pride ourselves on our commitment to excellence and our ability to solve complex IT challenges. Our team includes experts from ICSI, a leader in managed IT services, known for increasing IT and security maturity levels.

Essential Duties & Responsibilities:

• Diagnose and resolve technical issues, including Microsoft core business applications and operating systems.
• Deliver comprehensive troubleshooting and backend support to end users.
• Troubleshoot and resolve complex workstation issues and provide general server support.
• Perform initial triage for network degradation, outages, compromised accounts, and other critical technical incidents.
• Support Microsoft technologies such as Windows Server, Exchange, and SharePoint.
• Maintain and update system documentation within ConnectWise and IT Glue.
• Enhance customer satisfaction through high‑quality service and support.
• Ensure compliance with all company policies and procedures.
• Carry out additional duties as assigned by the supervisor.
• Participate in the on‑call rotation during non‑business hours.

Knowledge/Skills:

• Strong diagnostic and troubleshooting skills for a wide range of technical issues.
• Networking knowledge (DHCP, DNS, Wi-Fi setup, VLAN concepts).
• Strong knowledge with Microsoft 365, Entra ID/Azure AD, and user provisioning workflows.
• Solid understanding of Windows and macOS operating systems, networking fundamentals, and common business applications.
• Excellent analytical, problem‑solving, and communication skills.
• Ability to work independently as well as collaboratively within a team.
• Relevant certifications such as CompTIA A+, Network+, or Microsoft certifications are a plus.
• Strong customer service orientation with the ability to manage multiple tasks and adapt quickly to change.
• Prior experience with ConnectWise is a plus.

Experience with:

• Windows Server (2012+) / Active Directory
• Windows 10 & 11
• Office 365 / Microsoft 365 / Entra ID
• Backup solutions: Datto, Veeam
• Network/security: SonicWall, Cisco Meraki
• Security platforms: SentinelOne, Webroot, Barracuda, Avanan
• Mobile device management: Intune/MDM

Qualifications

• Proven experience in an IT support role, preferably within an MSP environment.
• Hands‑on experience with Microsoft 365, Exchange, and Active Directory.
• Experience supporting cloud environments (Azure, AWS, Google Cloud) is a plus.
• Demonstrated ability to diagnose and resolve technical issues efficiently and professionally.

Benefits/Perks

• Competitive compensation
• Fun, supportive workplace culture
• Pay commensurate with experience and qualifications
• Opportunities for career development and advancement
• Engaging, fast‑paced MSP environment

Physical Requirements:

• Regular, reliable attendance
• Ability to lift and carry up to 50 lbs
• Ability to communicate clearly over the phone