Help Desk Technician

GSD is hiring an onsite Help Desk L1 Agent in Hanover Park, IL to serve as the first line of support for clients in an MSP environment. In this role, you will troubleshoot technical issues across end-user devices, software, and networks while maintaining strong customer communication and clear documentation in ConnectWise.

You will handle incoming requests through phone, email, and the ConnectWise ticketing system, then either resolve problems directly or route more complex incidents to L2/L3 support. The work includes remote assistance when needed, occasional on-site support, and ongoing updates to technical documentation and knowledge base content.

Key Responsibilities

• Act as the first point of contact for clients via phone, email, and the ConnectWise ticketing system
• Diagnose and troubleshoot issues involving hardware, software, and network
• Provide front-line technical support and escalate complex issues to L2/L3 as needed
• Assist with installation, configuration, and maintenance of client IT systems
• Deliver remote and on-site support as required
• Maintain accurate, detailed records of client interactions in ConnectWise
• Create and update technical documentation and knowledge base articles
• Build client relationships through proactive support and follow-up
• Educate clients on IT best practices and preventive maintenance

Requirements

• Basic knowledge of the Microsoft 365 admin portal and application suite
• Basic understanding of Windows 10/11 (Mac not required)
• Basic knowledge of network infrastructure (modems, firewalls, VPNs, routers)
• Familiarity with remote support tools: TeamViewer, ScreenConnect, Bomgar
• Printer support experience, including installing and configuring network and local printers
• Basic understanding of antivirus/security tools including SentinelOne, Sophos, and FortiClient
• Outlook troubleshooting and connectivity skills
• Hardware troubleshooting experience with PCs, thin clients, laptops, and printers
• Familiarity with mobile devices, tablets, and 2FA applications
• Experience with ticketing systems such as ConnectWise, ServiceNow, or JIRA
• Excellent verbal and written communication, with the ability to explain technical concepts to non-technical clients
• Strong customer service skills across phone, email, and in-person interactions
• Solid analytical and systematic troubleshooting ability
• Effective time management and ability to juggle multiple support requests
• Collaborative mindset with willingness to share knowledge
• Adaptable to changing technologies and environments
• Composed under pressure, patient with clients, including during de-escalation scenarios
• Ownership of tasks with consistent follow-through
• High school diploma or equivalent; Associate’s degree in IT or related field preferred
• CompTIA A+, Network+, or similar certification preferred
• 1–2 years of technical support experience, ideally in an MSP help desk environment
• General familiarity with the ITIL framework and help desk best practices

Technologies

• Microsoft 365 admin portal
• Windows 10, Windows 11
• TeamViewer, ScreenConnect, Bomgar
• SentinelOne, Sophos, FortiClient
• ConnectWise, ServiceNow, JIRA
• ITIL

Schedule and Work Location

• Monday–Friday, 8am–5pm
• On-call rotation for after-hours support
• Occasional nights, weekends, or holidays as needed
• Occasional travel to customer sites
• Work location: In person

Compensation and Benefits

• Pay: $50,000.00 to $60,000.00 per year
• 401(k)
• 401(k) matching
• Dental insurance
• Health insurance
• Paid time off
• Professional development assistance
• Vision insurance