We are looking for a hands-on IT System Administrator to help support, maintain, and improve our internal IT infrastructure, business systems, and operations.
This role is a strong fit for a senior IT generalist who enjoys variety, ownership, and solving practical problems across different systems. You should be comfortable working in a fast-paced environment, supporting a growing technical team, and taking ownership of technical work with limited oversight.
You will work across Linux systems, Microsoft 365, identity and access management, networking, SaaS tools, automation, and internal business system integrations. You will also help strengthen our security posture, audit readiness, and compliance-related IT processes.
We are not looking for someone who is a deep specialist in every area. We are looking for someone with strong technical judgment, solid hands-on experience, and the ability to take ambiguous problems and drive them to practical solutions.
What Success Looks Like
In your first few months, you will begin taking ownership of assigned systems and projects, helping resolve complex technical issues, improving documentation, and supporting teammates.
Over time, you will help improve infrastructure maturity, strengthen security and compliance-related IT processes, automate repetitive work, and build practical integrations that help teams across the company operate more effectively.
A successful person in this role is curious, hands-on, security-minded, comfortable with ambiguity, and able to move work forward without needing every step defined in advance.
Key Responsibilities:
Own assigned IT services, workflows, and operational processes with limited oversight
Troubleshoot complex infrastructure, system, access, and application issues
Support employee onboarding and offboarding, access provisioning, system configuration, and lifecycle management
Coordinate operational changes and improvements across IT, Security, Engineering, business teams, and vendors
Maintain clear documentation for systems, procedures, standards, and changes
Mentor teammates, share knowledge, and help raise the technical bar of the team
Administer, maintain, and improve Ubuntu Linux servers and Windows-based environments
Manage Microsoft 365 services, including Entra ID, Exchange Online, SharePoint, Teams, access policies, groups, permissions, and identity workflows
Support endpoint management and device compliance through tools such as Intune
Monitor system health, performance, capacity, backups, and reliability
Investigate recurring issues, identify root causes, and implement lasting fixes
Support cloud and SaaS services, including access controls, configuration, integrations, monitoring, and routine administration
Support internal infrastructure across servers, networking hardware, cloud services, identity systems, and business applications
Troubleshoot switches, firewalls, VPNs, DNS, DHCP, routing, and internal connectivity
Perform basic network and firewall configuration where needed
Partner with Security and Engineering on infrastructure changes, network reliability, access controls, and operational requirements
Help identify gaps in monitoring, backup and recovery, reliability, and business continuity
Write and maintain scripts using Bash, Python, PowerShell, Ansible, or similar tools
Build and improve integrations between internal systems, SaaS tools, identity providers, and business workflows
Support workflow automation and internal productivity improvements for teams across the company
Help evaluate, deploy, and administer enterprise tools, collaboration platforms, and workflow integrations
Lead small improvement projects that strengthen reliability, documentation, compliance readiness, or team efficiency
IT Operations and Service Ownership, 40%
Systems, Identity, and Cloud Administration, 30%
Networking and Infrastructure, 15%
Automation, Integrations, and Improvement, 15%
Required Skills & Qualifications:
4+ years of experience in systems administration, infrastructure, internal IT operations, managed services, or a related technical role
Ability to own assigned systems, services, or projects with limited oversight
Strong Ubuntu or Linux administration experience, including troubleshooting services, logs, permissions, packages, storage, certificates, and networking
Hands-on experience with Microsoft 365, Entra ID, Exchange Online, SharePoint, Teams, access management, groups, permissions, SSO, Conditional Access, and enterprise applications
Experience supporting endpoint management or device compliance, such as Intune
Practical networking knowledge of DNS, DHCP, TCP/IP, routing, firewalls, VPNs, and internal connectivity
Experience writing scripts or automations using Bash, Python, PowerShell, Ansible, or similar tools
Experience supporting SaaS tools, APIs, workflow automation, or business system integrations
Ability to support secure IT operations, access controls, audit readiness, and compliance-related work
Ability to mentor teammates, share knowledge, and improve team practices
Clear written and verbal communication, including the ability to explain technical decisions, risks, trade-offs, and recommendations
Bonus Points:
Experience in a managed service provider, small company, or small technical team environment
Experience supporting audit readiness, security reviews, access reviews, or compliance-related IT requirements
Experience working in security-conscious or compliance-conscious environments
Ability to meet applicable background screening or clearance requirements, where required
Experience with AWS services such as EC2, S3, IAM, VPC, CloudWatch, or Systems Manager
Familiarity with Terraform, Ansible, CloudFormation, or similar tools
Experience managing switches, firewalls, VPN appliances, or wireless infrastructure
Experience building automations using APIs, webhooks, vendor documentation, or integration tools
Kepler Communications Toronto, Ontario, CAN Office
196 Spadina Avenue, , , Toronto, Ontario, Canada, M5T2C2
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