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Level 2 Support Specialist
Oshawa, ON
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Job Title: Level 2 Escalation Technician


Location: Durham Region, ON (Hybrid: WFH & Field)

Job Type: Full-Time

Compensation: $70,000.00 - $90,000.00 

PTO: 3 weeks

Working Style: Hybrid / Field; work from home with approx 1-2 client site visits per week

Certifications/Training: Employer Paid*


About Us

Our Client is a growing Managed Service Provider (MSP) based in the Durham Region. We pride ourselves on delivering top-tier IT support, strategic guidance, and secure infrastructure to our clients. We are looking for a dedicated IT professional who is passionate about technology and eager to grow their career with a team that values expertise and customer success.


The Role

We are seeking a highly skilled Level 2 Escalation Technician to join our team. In this role, you will serve as the primary escalation point for complex technical issues that our Level 1 team cannot resolve. Your core focus will be on network infrastructure (firewalls, switches, Wi-Fi), Microsoft 365 environments, and virtualization. This is a dynamic, hybrid position. You will spend the majority of your time working remotely from home, with the requirement to travel to client sites within the Durham Region (and surrounding areas) 1 to 2 times per week for hands-on troubleshooting, deployments, and face-to-face client support.


Key Responsibilities

  • Escalation Support: Act as the primary escalation point for Level 1 technicians, resolving complex technical issues efficiently.
  • Network Management: Configure, troubleshoot, and maintain network infrastructure, including firewalls (SonicWall, WatchGuard), switches, and wireless access points (Ubiquiti).
  • Cloud & Systems Administration: Manage, deploy, and troubleshoot Microsoft 365 environments (Exchange Online, SharePoint, Teams, Entra ID/Azure AD).
  • Virtualization: Deploy, manage, and troubleshoot virtualized environments using VMware ESXi and/or Microsoft Hyper-V.
  • RMM Management: Utilize Datto RMM, Field Effect to monitor client networks, manage alerts, deploy scripts, and maintain accurate documentation of environments and ticket resolutions.
  • Client-Facing Support: Travel to client locations 1 to 2 times per week to perform onsite diagnostics, hardware installations, and build strong relationships with users and stakeholders.
  • Mentorship: Provide technical guidance and share knowledge with junior technicians to elevate the team's overall capabilities.


Required Qualifications

  • MSP Experience: previous, proven experience working within a Managed Service Provider environment.
  • Vehicle Requirement: a valid G-class driver’s license, a clean driving record, and access to a reliable personal vehicle for client visits (mileage will be compensated).
  • Technical Proficiency: strong working knowledge of ConnectWise (Manage).
  • Hands-on experience configuring and supporting SonicWall, WatchGuard, and Ubiquiti networking gear.
  • Solid understanding of server virtualization (ESXi and Hyper-V).
  • Deep knowledge of Microsoft 365 administration and troubleshooting.
  • Professionalism: exceptional written and verbal communication skills. You must be comfortable and confident speaking directly with clients and translating technical jargon into plain English.
  • Dedication: we are looking for someone truly dedicated to their IT profession who takes ownership of issues from start to finish.


What We Offer

  • Career Growth: This role offers a fantastic career path for the right individual who wants to eventually move into Leadership
  • Work-Life Balance: Enjoy the flexibility of working from home 3 to 4 days a week.
  • Compensation: Competitive salary, vehicle/mileage allowance, and comprehensive benefits package [adjust as needed].
  • Continuous Learning: Opportunities for training and certifications to keep your skills sharp in a fast-changing industry.



Top Tier Talent Group is committed to diversity, equity, and inclusion in staffing, recognizing that diversity in backgrounds, identities, abilities, and perspectives drive innovation and create inclusive workplaces. We make every effort to attract, retain, and empower talent from all communities and experiences ensuring full and fair consideration for candidates. 


If you are a candidate who requires accommodations during the recruitment process, please let us know.



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