Junior Help Desk Technician (Level 2) - Remote

Are you an experienced IT support professional ready to take the next step in your career? As a Level 2 IT Support Technician, you will play a critical role in diagnosing and resolving complex technical issues while supporting both end users and junior technicians. This fully remote role is ideal for someone who thrives in a fast-paced MSP environment and enjoys solving challenging problems across multiple client environments.

You will work closely with Level 1 technicians, assisting with escalated tickets, troubleshooting infrastructure issues, and helping maintain secure and reliable IT systems. This role provides the opportunity to deepen your expertise in Microsoft environments, networking, cloud systems, and security while supporting healthcare organizations that rely on technology to operate effectively.

If you enjoy tackling complex problems, mentoring junior technicians, and working with a wide variety of technologies, this role offers an excellent path toward senior engineering or infrastructure roles.

What You'll Do

• Troubleshoot and resolve escalated Level 1 tickets involving Windows systems, Microsoft 365, networking, and cloud environments
• Support and maintain Active Directory, Azure AD, Microsoft 365, and user identity management
• Diagnose and resolve network connectivity issues, VPN problems, and firewall-related issues
• Manage and maintain servers, virtual machines, and core infrastructure components
• Perform advanced troubleshooting of workstation, server, and application issues
• Assist with Microsoft 365 administration including Exchange Online, SharePoint, and Teams
• Document troubleshooting steps, resolutions, and system changes within Autotask PSA
• Participate in client onboarding, system deployments, and infrastructure upgrades
• Collaborate with Level 1 technicians by providing guidance and technical support
• Follow defined ticket prioritization and SLA response standards
• Maintain strict HIPAA and security compliance when handling client data
• Deliver professional, high-quality support to both technical and non-technical users

• 3+ years of IT support experience, preferably in an MSP environment
• Strong experience with Windows Server and Windows 10/11 administration
• Solid knowledge of Microsoft 365 administration and Azure AD
• Experience troubleshooting networking issues (DNS, DHCP, VPN, TCP/IP)
• Familiarity with Active Directory, Group Policy, and user identity management
• Strong troubleshooting and analytical skills
• Excellent communication and documentation skills
• Ability to manage multiple tickets and priorities in a fast-paced MSP environment
• Reliable home office setup with high-speed internet

Preferred (Nice-to-Have)

• CompTIA Network+, Security+, or Microsoft certifications
• Experience with Datto RMM, Autotask, or other MSP toolsets
• Experience managing firewalls, VPNs, and network infrastructure
• Virtualization experience (Hyper-V or VMware)
• Healthcare IT or HIPAA-regulated environment experience
• Prior MSP experience supporting multiple client environments

Tools You'll Use

• Datto Autotask PSA
• Remote Monitoring & Management (RMM) tools
• Remote desktop/support tools
• Windows Server and Microsoft 365 environments
• Active Directory / Azure AD
• Networking and security tools

Pulled from the full job description

• Paid training
• 401(k)
• Health insurance
• Paid time off
• Vision insurance
• Health savings account
• Dental insurance, * Medical, dental & vision insurance
• 401(k)
• Paid time off & holidays
• Paid training and certification reimbursement
• Fully remote work environment
• Clear growth path to Level 3 Engineer / Systems Engineer, * 401(k)
• Dental insurance
• Health insurance
• Health savings account
• Life insurance
• Paid time off
• Vision insurance