Job Description

Overview

The Level 3 IT Support Specialist serves as a senior technical resource within our Managed Services team, responsible for resolving the most complex technical issues, mentoring junior staff, and providing strategic input on system architecture and project implementations. This role requires deep technical expertise across infrastructure, cloud platforms, and security, with a focus on delivering exceptional service to our clients while supporting business continuity, cybersecurity, and modern workplace enablement.

Key Responsibilities

Act as the final point of escalation for complex infrastructure, networking, cloud, and security issues. Provide expert-level support for Windows Server, Microsoft 365 (including Exchange, Intune, SharePoint, and Teams), Azure AD, and on-premise AD environments. Lead advanced troubleshooting across endpoints, servers, virtual environments (VMware/Hyper-V), networking, and security appliances (Fortinet, WatchGuard, Cisco). Architect and lead the deployment of infrastructure and cloud-based solutions for client projects, including migrations, upgrades, and security improvements. Review and resolve critical alerts from RMM and SIEM platforms, including patching, backup failures, antivirus, and firewall alerts. Develop and maintain technical standards, configuration baselines, and documentation. Provide mentorship and guidance to Level 1 and Level 2 support staff. Identify recurring problems and design long-term solutions to eliminate root causes. Lead or assist in security incident response, vulnerability assessments, and remediation. Perform infrastructure assessments and audits for client environments and provide written reports and recommendations. Participate in the on-call rotation and after-hours maintenance or project work when required. Excellent communication, documentation, and customer service skills. Proven ability to lead technical projects and mentor junior team members. Strong analytical thinking and time management skills.

Required Qualifications

Bachelor's degree in Information Technology or equivalent experience. 5+ years of progressive IT support experience, preferably in an MSP or fast-paced enterprise environment.
Multiple relevant certifications strongly preferred:

Microsoft 365: MS-102, SC-300, or equivalent Azure Administrator Associate (AZ-104) Fortinet NSE 4+ or WatchGuard Advanced Certifications VMware VCP or equivalent virtualization certification
Deep knowledge of:

Windows Server 2012-2022, Active Directory, Group Policy, DNS, DHCP Microsoft 365 suite including Exchange Online, SharePoint, Teams, Intune, Defender for Endpoint Azure AD, hybrid identity setups, and conditional access policies Firewalls, VPNs, and network architecture (Fortinet, WatchGuard, Cisco Meraki) Backup and DR solutions (e.g., Veeam, Datto) PowerShell scripting and automation
Job Type: Full-time

Pay: $33.65-$38.46 per hour

Expected hours: 40 per week

Additional pay:

Overtime pay
Benefits:

Extended health care Mileage reimbursement On-site parking Paid time off
Schedule:

Monday to Friday On call Overtime
Ability to commute/relocate:

Whitby, ON L1N 2C3: reliably commute or plan to relocate before starting work (required)
Work Location: Hybrid remote in Whitby, ON L1N 2C3