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