Junior Systems Administrator / Operations… at Upstaff · Toronto

Position Overview

We are seeking a motivated and technically capable Junior Systems Administrator / Operations Support Specialist to provide day-to-day systems administration, IT infrastructure support, and operational assistance within a large enterprise IT environment.

The successful candidate will support Windows-based infrastructure, user account administration, server and workstation operations, network connectivity, cloud services, security practices, and IT service management activities.

This role requires someone with strong troubleshooting abilities, a customer-focused approach, and the ability to work collaboratively with technical teams while ensuring timely resolution of incidents and service requests.

The ideal candidate will have hands-on experience providing Level 1 and Level 2 technical support, administering user accounts and access permissions, troubleshooting hardware and software issues, and supporting enterprise IT environments.

Key Responsibilities

• Provide day-to-day systems administration and operational support for enterprise IT infrastructure, including servers, workstations, networks, and related services.
• Configure and maintain user accounts, user profiles, access permissions, and security settings.
• Support Microsoft Windows Server environments, including Active Directory, Group Policy, DNS, DHCP, and user account management.
• Perform system installations, software upgrades, patch deployments, routine maintenance, and configuration changes.
• Troubleshoot hardware, software, network connectivity, and system performance issues using structured diagnostic and problem-solving methodologies.
• Monitor system performance, computer workload trends, and infrastructure utilization to help maintain optimal system availability and performance.
• Support enterprise infrastructure components, including file servers, print services, virtualization platforms, and endpoint management solutions.
• Assist with Microsoft Azure, Microsoft 365, Entra ID (Azure AD), and related cloud-based identity and administration services.
• Support backup, recovery, and routine system maintenance activities to ensure operational continuity.
• Apply cybersecurity best practices, including account security, patch management, vulnerability remediation, endpoint protection, and access control.
• Support network infrastructure and connectivity, including TCP/IP, VPNs, firewalls, and enterprise network troubleshooting.
• Utilize IT Service Management (ITSM) platforms such as ServiceNow, Remedy, or similar tools to manage incidents, problems, changes, and service requests.
• Perform basic scripting and automation using PowerShell, batch scripting, or similar technologies to improve operational efficiency.
• Maintain technical documentation, knowledge articles, operational procedures, and system inventories.
• Coordinate with internal technical teams, vendors, and business stakeholders to resolve infrastructure and application-related issues.
• Follow established IT operational procedures, security standards, and change management processes.
• Provide timely updates to stakeholders and ensure incidents and service requests are resolved within established Service Level Agreements (SLAs).
• Participate in scheduled maintenance activities and after-hours operational support when required.

Mandatory Technical Skills and Qualifications

Candidates must demonstrate the following technical knowledge and capabilities:

1. Knowledge of Microsoft Windows Server administration, including Active Directory, Group Policy, DNS, DHCP, and user account management.
2. Experience supporting enterprise infrastructure environments, including file servers, print services, virtualization platforms (VMware or Hyper-V), and endpoint management solutions.
3. Understanding of cloud technologies and administration, preferably Microsoft Azure, Microsoft 365, Entra ID (Azure AD), and related identity management services.
4. Knowledge of IT Service Management (ITSM) processes, including incident, problem, change, and service request management using ServiceNow, Remedy, or similar platforms.
5. Ability to troubleshoot hardware, software, network connectivity, and system performance issues using structured diagnostic methodologies.
6. Understanding of cybersecurity best practices, including account security, patch management, vulnerability remediation, endpoint protection, and access control.
7. Basic scripting and automation skills using PowerShell, batch scripting, or similar technologies.
8. Knowledge of networking fundamentals, including TCP/IP, VPNs, firewalls, network troubleshooting, and enterprise connectivity concepts.
9. Understanding of backup and recovery processes, user access administration, and day-to-day computer systems operations.
10. Familiarity with one or more operating systems, hardware platforms, information retrieval packages, communications protocols, middleware, and gateways.

Requirements

Required Experience

• Experience providing Level 1 and Level 2 technical support within a medium to large enterprise environment.
• Experience monitoring, maintaining, and supporting server, workstation, and network infrastructure with minimal supervision.
• Demonstrated experience resolving technical incidents and service requests while meeting established SLAs.
• Experience performing system administration activities, including user provisioning, access management, software installation, patch deployment, and system maintenance.
• Experience working within a structured IT operational environment with documented processes, standards, and change management procedures.
• Experience supporting business-critical applications and coordinating issue resolution with technical teams and external vendors.
• Experience preparing and maintaining technical documentation, knowledge articles, operational procedures, and system inventories.
• Experience with backup and recovery, system operations, and infrastructure maintenance.

Mandatory Communication and Interpersonal Skills

• Strong verbal communication skills, with the ability to explain technical concepts and solutions to both technical and non-technical stakeholders.
• Demonstrated customer service orientation, with a focus on professionalism, responsiveness, and client satisfaction.
• Ability to clearly document incidents, troubleshooting activities, resolutions, and technical procedures.
• Strong interpersonal skills and the ability to establish effective working relationships across operational, technical, and business teams.
• Ability to prioritize competing requests, provide timely status updates, and manage stakeholder expectations in a fast-paced environment.
• Demonstrated ability to work collaboratively within a team while independently managing assigned responsibilities.
• Strong analytical, problem-solving, and decision-making skills.

Key Mandatory Requirements – Client's Must-Haves

Candidates must clearly demonstrate the following five capabilities in their resumes:

1. Technical Troubleshooting: Ability to troubleshoot hardware, software, network connectivity, and system performance issues using structured diagnostic methodologies.
2. Cybersecurity Knowledge: Understanding of cybersecurity best practices, including account security, patch management, vulnerability remediation, endpoint protection, and access control.
3. Cloud Technologies: Understanding of cloud technologies and administration, preferably Microsoft Azure, Microsoft 365, Entra ID (Azure AD), and related identity management services.
4. Strong Verbal Communication: Ability to explain technical concepts and solutions effectively to both technical and non-technical stakeholders.
5. Customer Service Orientation: Demonstrated commitment to professionalism, responsiveness, and client satisfaction.

Desirable Skills

• Experience supporting distributed and networked systems.
• Awareness of emerging IT trends, technologies, and infrastructure practices.
• Experience with one or more programming or scripting languages.
• Knowledge and understanding of the Accessibility for Ontarians with Disabilities Act (AODA), related regulations, and accessibility standards.
• Experience with VMware or Hyper-V virtualization technologies.
• Experience participating in after-hours support, scheduled maintenance, or operational on-call rotations.

Ideal Candidate Profile

The ideal candidate will be a junior-level IT professional with practical experience in enterprise IT support and systems administration. The candidate should possess a solid understanding of Windows infrastructure, cloud technologies, cybersecurity fundamentals, and networking.

We are particularly interested in candidates who are:

• Hands-on in troubleshooting hardware, software, server, and network-related issues.
• Familiar with Microsoft infrastructure and cloud administration.
• Knowledgeable in IT security, user access management, and patching practices.
• Customer-oriented with excellent communication and documentation skills.
• Comfortable working in a structured enterprise IT environment.
• Able to work independently while collaborating effectively with infrastructure and operations teams.