System Support Specialist

Job Title: Microsoft 365 / Systems Support Specialist

Job Type: 4-Week Contract (possibility of extension)

Location: 100% Remote (Markham, ON)

Duration: 4 Weeks (Approx. 240 Hours)

Schedule: Monday – Friday | 40 Hours/Week

Start Date: ASAP

Rate : $70/hr T4 OR $85/hr Inc.

About the Opportunity

Our client is seeking an experienced Microsoft 365 / Systems Support Specialist to join their IT team on a short-term contract. This is an excellent opportunity for a Microsoft infrastructure professional who thrives in both cloud and on-premises environments and enjoys solving complex technical issues. Working remotely, you will provide hands-on technical support and administration across Microsoft 365 services, Azure, and enterprise Microsoft infrastructure while ensuring users experience reliable, secure, and efficient collaboration services.

Key Responsibilities

  • Provide technical support and troubleshooting across Microsoft 365 and enterprise Microsoft technologies.
  • Administer and support Exchange Online, including mailbox management, issue resolution, and configuration.
  • Support SharePoint Online, OneDrive for Business, and Microsoft Teams environments.
  • Administer and troubleshoot Microsoft Entra ID (Azure Active Directory).
  • Support Enterprise Mobility + Security (EMS) technologies.
  • Troubleshoot and support on-premises Exchange, Active Directory, SharePoint, and Skype for Business environments.
  • Perform certificate renewals, refreshes, and related infrastructure tasks.
  • Diagnose and resolve authentication, access, connectivity, and application issues.
  • Collaborate with internal IT teams to resolve complex technical incidents.
  • Document troubleshooting activities, resolutions, and technical procedures.
  • Deliver exceptional technical support while managing multiple priorities in a fast-paced environment.
Required Skills & Experience
  • Strong hands-on experience supporting Microsoft 365 enterprise environments.
  • Expertise with Microsoft Exchange Online, SharePoint Online, OneDrive for Business, Microsoft Teams, Microsoft Entra ID (Azure Active Directory), Enterprise Mobility + Security (EMS)
  • Experience supporting on-premises Microsoft technologies, including Exchange Server, Active Directory, SharePoint Server, Skype for Business
  • Experience performing certificate management and certificate refreshes.
  • Strong troubleshooting skills across Microsoft cloud and on-premises infrastructure.
  • Excellent analytical and problem-solving abilities.
  • Strong communication skills with both technical and non-technical stakeholders.
  • Ability to work independently in a remote environment with minimal supervision.
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