Help Desk Technician Tier 2

International Computer Sciences Inc; Annapolis (MD); On-site; USD 45,000 - 65,000; Full time

Benefits offered by this job

401(k) matching

Bonus based on performance

Company car

Dental insurance

Health insurance

Paid time off

Training & development

Job summary

A leading Managed Service Provider is seeking a Help Desk Technician – Tier 2 in Annapolis, MD. The role involves diagnosing technical issues, supporting Microsoft technologies, and enhancing customer satisfaction. Applicants should have relevant certifications and experience in an IT support role, prepared to work in a dynamic MSP environment. Benefits include 401(k) matching, competitive salary, and opportunities for advancement.

Qualifications

• Proven experience in an IT support role, preferably within an MSP environment.
• Hands-on experience with Microsoft 365, Exchange, and Active Directory.
• Demonstrated ability to diagnose and resolve technical issues efficiently.

Responsibilities

• Diagnose and resolve technical issues, including Microsoft core business applications.
• Support Microsoft technologies such as Windows Server and Exchange.
• Enhance customer satisfaction through high-quality service.

Skills

Diagnostic and troubleshooting skills

Networking knowledge (DHCP, DNS, VLAN)

Knowledge with Microsoft 365

Analytical and problem-solving skills

Strong customer service orientation

Education

Relevant IT certifications (CompTIA A+, Network+)

Proven experience in an IT support role

Tools

ConnectWise

Microsoft Exchange

Windows Server (2012+)

Backup solutions (Datto, Veeam)

Security platforms (SentinelOne, Webroot)

Job description

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

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.

Physical Requirements

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