IT Systems Support Specialist

IT Systems Support Specialist

At Odyssey Trust Company, we do things differently. Our core mission is to provide peace of mind to our clients by making things simple, fast, and easy.

Odyssey is a tight-knit, solution-driven team. Our shared values, as defined by our own employees, guide us in reaching our individual and collective goals:

• We Show Up for Each Other: We are in this together! We collaborate and support each other to get results. Our employees are compensated with competitive salaries and a comprehensive benefits package.
• We Build: "Outside the box” is our playground. We’re not afraid to innovate and tackle tough problems – we’re here to disrupt the industry. Creativity and problem-solving is not reserved for the Executive team.
• We Get Stuff Done (GSD): We have a notable reputation for being exceptionally responsive. Coming up with a great idea is only part of the solution; We take great ideas and put them into action.
• We Do the Right Thing: We’re dependable, trustworthy, and proud of our professional standards.

Primary Responsibilities & Attitude

We’re looking for an IT Systems Support Specialist to join our growing company, Odyssey Trust! Our ideal candidate is someone who loves IT and wants to work with a great group of people. The candidate will be known for their work ethic and “can do” attitude and consider themselves to be a team player.

The candidate will report to our Managing Director, IT and work on a hybrid schedule, with the expectation of being in-office two days per week. We pride ourselves on having a team that is knowledgeable, friendly, and always willing to support each other.

You are responsible for:

• Providing technical support to end-users across the organization in a timely and positive manner
• Troubleshoot, install, configure, and maintain hardware and software
• Manage and prioritize incidents and service requests in the ticketing system
• Escalate complex issues to the Managing Director, IT, or to external vendor/support partners as needed
• Document and update knowledge base articles and procedures
• IT inventory tracking
• Ensuring endpoints and servers are kept up to date
• User account provisioning/deprovisioning (onboarding & offboarding, M365/Entra ID, access/permissions)
• Basic network administration (Wi-Fi, switches, VPN, troubleshooting connectivity)
• Mobile device management (phones/tablets, MDM/Intune enrollment)
• Backup/disaster recovery checks
• Vendor and ISP liaison work
• Providing occasional after-hours or weekend support for maintenance windows, patching or outages.
• Maintaining confidentiality and exercising sound judgement when handling sensitive company and client data

Skills and Experience:

• Diploma in Computer Science and/or Systems (or equivalent combination of education and experience)
• 3 years’ experience minimum
• Experience troubleshooting and resolving technical issues
• Ability to work independently, self-motivated and self-starter
• Experience with Entra ID, Intune, Exchange Online, Windows 11 and PowerShell.
• Strong knowledge of Windows operating systems, Microsoft Office Suite, and Microsoft 365 administration.
• Possess the ability to clearly communicate technical problems and generate solutions.
• Have a professional and positive attitude with a solution-based approach to challenges.
• Strong critical thinking and decision-making skills.
• Must be authorized to work in Canada.
• Relevant certifications (e.g. CompTIA A+, Network+, Microsoft certifications) considered an asset.
• Experience managing endpoints in Financial Services, FinTech, Banking, Insurance or another regulated environment is also considered an asset.

What We Offer:

Paid Time Off: Vacation, Flex Days, Bonus Day and Birthday Day off

Benefits: Extended Health, Dental, Life Insurance, ADD, Critical Illness, Long Term Disability, Employee Assistance Program, $500 Health Care Spending/Lifestyle Spending Account, RRSP/TSFA Match.

We thank all candidates for their interest; however, only those selected for an interview will be contacted. By submitting your resume, you consent to the collection, use and necessary disclosure of the personal information provided during the application and selection process.

We welcome and encourage applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the selection process.