Help Desk Technician Tier 2
Annapolis
Help Desk Technician Tier 2
Full Time • Annapolis
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.
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
Compensation: $70,000.00 per year
Managed IT Services in Maryland, Virginia, Washington DC, Delaware, Pennsylvania, and Florida since 1987
Established in 1987 and headquartered in Annapolis, Maryland, ICSI is a Managed IT Services and Consulting firm. Cities in Maryland, Virginia, Washington DC, Delaware, Pennsylvania and Florida that we serve include: Annapolis, Arlington, Alexandria, Baltimore, Beltsville, Bethesda, Bowie, Catonsville, Clinton, College Park, Columbia, Falls Church, Fairfax, Frederick, Greenbelt, Harrisburg, Hyattsville, Johnstown, McLean, Reston, Rockville, Scranton, Silver Spring, Tampa, Vienna, Washington, DC, and York
We provide Managed IT Services to various industries in Maryland, Virginia, Washington DC, Delaware, Pennsylvania and Florida, including Medical Practices, Non-Profit Organizations, Real Estate Offices, Construction Firms, Consulting Agencies, and Engineering Groups.
ICSI Business Principles
At ICSI, we are committed to bringing excellence to the Managed IT Services industry via our IT staffing and software partnerships. We employ the highest levels of quality in our solutions.
One of our strategic solutions is to address the client’s requirements and maximize the productivity of their assets. We provide talented, service-oriented consulting professionals who will assist in implementing our commercial and residential client’s goals.
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