Senior IT Support Specialist

Senior IT Support Specialist

12 Month Contract Position

About Cloud Metric

We’re a rapidly growing technology services company (Cloud Metric, Telecom Metric, Server Cloud Canada), delivering AI, cloud infrastructure, IT managed services, cybersecurity, and VoIP solutions to 200+ clients across Canada. We are founded on the principle of putting customers first, and investment in our team.

Core Values

• Customer First
• Honesty & Integrity
• Growth Mindset
• One Team, One Mission
• Ownership
• Resiliency

About the Role

We’re looking for a Senior IT Support Specialist who excels at solving complex technical problems and strengthening the overall support experience. In this role, you’ll take ownership of challenging issues that require broader system awareness—such as identity, networking, and multiservice interactions—while helping create clarity, consistency, and confidence across the support team.

You’ll work hands on with escalated or advanced issues, transform real world experience into practical documentation and training, and help guide support practices as the team evolves toward more collaborative problem solving approaches. This is a great fit for someone who enjoys digging into tricky problems, understanding how systems connect, and improving how teams work together.

Why this role exists (12-month contract)

You will act as the bridge between Tier 1 and Tier 2 by owning escalations from Tier 1, unblocking tricky technical issues, and escalating to Tier 2 when deeper engineering expertise is required. Over time, success means fewer escalations are needed because the team’s skills and knowledge base improve.

Success looks like (first 90 days)

• You become a reliable escalation path for Tier 1 and help maintain consistent, customer-first communication on complex issues.
• You establish a steady rhythm of knowledge transfer between Tier 2 and Tier 1 through short trainings, shadowing, and “teach-back” sessions.
• You improve how solutions are captured and reused by strengthening knowledge management practices (for example, clearer KB standards, better troubleshooting runbooks, and closing the loop after incidents).
• You help shift support capacity so Tier 2 can spend more time on implementations and projects, while Tier 1 becomes more confident handling recurring problem areas independently.

A core measure of success is that the team becomes more self-sufficient over time through better training, documentation, and repeatable troubleshooting patterns.

What You’ll Do

Advanced Technical Support

• Lead the investigation and resolution of complex support issues requiring deeper troubleshooting across systems, identity, networking, or service dependencies.
• Manage issues from start to finish, providing clear communication and reliable outcomes.
• Identify patterns or recurring problems and recommend improvements to reduce future incidents.
• Collaborate with peers when shared problem solving adds value, and work with specialists or engineering teams when deeper expertise is required.

Knowledge Sharing & Team Enablement

• Translate advanced troubleshooting steps into clear, useful documentation and internal guides.
• Deliver training sessions that help others gain confidence handling more complex issues.
• Maintain and improve the knowledge base, ensuring content is accurate, accessible, and actionable.
• Work with the support team to identify knowledge gaps and proactively close them.

Service & Process Improvement

• Contribute to efforts that improve support workflows, documentation quality, and consistency.
• Participate in major incident response and ensure that learnings are captured and shared.
• Support the adoption of new tools, processes, and best practices that enhance service quality.

What You Bring

• 5+ years of progressively advanced IT support experience.
• Postsecondary education in a relevant field (preferred).
• Strong written and verbal communication skills
• Customer satisfaction focused mindset.
• Ability to quickly learn new systems, tools, and workflows.
• Experience creating documentation, sharing technical knowledge, or delivering training.
• Familiarity with major incident management and root cause analysis.
• Strong analytical skills with the ability to identify trends across support activity.
• Excellent organization, prioritization, and time management.
• Ability to influence and collaborate without formal authority.
• Willingness to participate in on call rotation and occasional afterhours work.
• Familiarity with knowledge centered support practices (KCS) is a plus.

Technical Expertise

This role requires hands on experience or demonstrated troubleshooting ability within the following areas:

• Virtualization & hosting: VMware vSphere or Proxmox (KVM/LXC), plus familiarity with common storage backends (SAN, vSAN, Ceph) and cloud environments (Azure).
• Networking & perimeter security: TCP/IP fundamentals, VLANs and routing, VPNs, segmentation, and firewall administration (pfSense/OPNsense-class and comparable SMB/enterprise firewalls).
• Microsoft cloud & identity: Azure and Entra ID (Azure AD), and core M365 administration (Exchange, SharePoint, Teams, security/compliance basics, user and license management).
• Systems administration & automation: Windows Server, Active Directory and Group Policy, Linux fundamentals, and scripting for support/triage (PowerShell, Bash).
• Monitoring, RMM, and endpoint management: RMM tooling, alert triage, patching, and device management (including Intune).
• Backup & disaster recovery: Veeam-based backup/replication and restore troubleshooting, plus experience with MSP-style backup platforms (for example, Cove or Acronis).
• Security tooling (support/operations): Endpoint protection and EDR concepts, email security, MFA, and vulnerability/awareness tooling from a “respond and remediate” perspective.
• Automation and integrations: Workflow automation (n8n-class tooling) and working with APIs/webhooks to connect systems.
• Voice/telephony (as applicable): Teams voice/SBC concepts and VoIP monitoring basics.

Interview Process

1st Stage

If we feel there is a match with an applicant, we will move them forward to a 1st stage interview, where we will focus on our core values and the candidate’s alignment with them, whilst also assessing potential for future growth. In addition, it will be an opportunity to bring forward what they are looking for in an employer. This interview is an informal introductory conversation.

If there is a match at this stage, then the candidate will be moved to a second interview.

2nd Stage Interview

This stage will focus more on the technical aspects of the role and the specific technical and skill needs. The interview will include more structured questions.

If there is a continued match at this stage, then the candidate will be moved to a final interview.

Final Stage Interview

This final interview will be an opportunity for the candidate to bring forward their thoughts on how they would approach the new role for the first 30, 60, and 90 days, and how they feel they will be able to impact the business.

Our Promise to Candidates

We are always humbled to receive applications, and we also recognize that job hunting is tough and takes a lot of time and energy. It can often be a stressful time, not made easier when the process is not made clear. We promise all candidates that we will acknowledge the receipt of applications, and that all resumes and cover letters will be reviewed in full by a human and not a machine!

We promise to update all candidates at each stage of the process. If invited to the interview process, we make a commitment that the whole process will take no longer than 2–4 weeks, and that if we decide not to progress your application further at any stage we will communicate that at the earliest possible opportunity.

We strongly believe that all applicants should be treated with respect throughout the process, whatever the outcome of the application.

Cloud Metric is an equal opportunity employer committed to diversity, equity, and inclusion. We welcome applications from all qualified candidates regardless of race, gender, age, religion, sexual orientation, or any other protected characteristic.

Job Type: Fixed term contract

Contract length: 12 months

Pay: $70,000.00-$80,000.00 per year

Benefits

• Casual dress
• Dental care
• Extended health care
• Life insurance
• On-site parking
• Paid time off

Experience

• IT support: 5 years (preferred)
• Telephony Support: 5 years (preferred)
• RMM Endpoint Management: 5 years (preferred)
• M365 Support: 5 years (preferred)

Location:

• Kingston, ON K7L 2L1 (preferred)

Work Location: In person