Level 2 Help Desk Specialist

STACK IT Recruitment

17h • $60,000 - $70,000 • Remote

About The Position

Do you thrive in fast-paced environments where solving complex technical problems and supporting clients go hand in hand? We’re looking for an L2 Help Desk Specialist who thrives in a fast-paced MSP environment and enjoys tackling complex technical challenges across a variety of client environments. This is a hands-on, high-impact role where you’ll work across infrastructure, cloud, and end-user systems, owning issues end-to-end and contributing to long-term solutions, not just quick fixes. This is an opportunity to join a team that values curiosity, accountability, and continuous improvement, where your technical voice is heard, and your growth is actively supported.

A strong IT support professional with experience handling Level 2 escalations in a dynamic environment Someone who enjoys digging into root causes, not just resolving surface-level issues Comfortable working directly with clients and building trusted relationships A team player who supports others while taking ownership of your work Naturally curious, always looking to learn new technologies and improve systems Calm under pressure, organized, and able to manage multiple priorities effectively

Requirements

• 3+ years of hands-on IT support experience, ideally within an MSP or multi-client environment
• Strong technical foundation across Microsoft environments, including Active Directory (on-prem & Azure/Entra ID), Microsoft 365, and Exchange Online
• Proven experience in troubleshooting server, desktop, and network issues in a fast-paced support setting
• Solid understanding of virtualization technologies (VMware and/or Hyper-V)
• Working knowledge of networking fundamentals, including TCP/IP, firewalls, and security troubleshooting
• Experience with cloud platforms and modern endpoint management tools (Intune, Azure, O365 ecosystem)
• Familiarity with RMM, PSA tools, and system monitoring platforms
• Exposure to backup and disaster recovery processes across client environments
• Strong analytical and root-cause problem-solving skills, with the ability to manage and resolve escalated issues effectively
• Excellent communication skills with a client-first mindset, comfortable acting as a trusted technical point of contact
• A collaborative team player who can support and mentor Level 1 technicians when needed
• Highly organized, adaptable, and able to perform under pressure in a dynamic environment

Responsibilities

• Act as an escalation point for Level 1 technicians, resolving complex desktop, server, and network issues within SLA expectations
• Troubleshoot and support Microsoft environments, including Active Directory, Office 365, Azure/Entra ID, and Exchange Online
• Diagnose email and connectivity issues (SMTP, POP, IMAP, network-related problems)
• Support virtualization platforms such as VMware and Hyper-V
• Handle networking and security troubleshooting (TCP/IP, firewalls, access issues)
• Contribute to project work, including system migrations, cloud transitions, and infrastructure improvements
• Assist with backup and disaster recovery planning and execution for client systems
• Continuously identify opportunities to improve systems, processes, and client environments

Benefits

• Base Salary: $60,000 - $70,000
• Paid Time Off: Competitive vacation and personal days to maintain a healthy work-life balance
• Benefits Package: Medical, dental, and vision benefits to support your overall well-being
• RRSP Matching: Employer contributions to a group RRSP program, supporting your long-term financial security

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 1-10 employees