Junior Systems Administrator / MSP Technical Support Specialist
Location: Ontario, Canada
Employment Type: Full-Time
Ready to Take the Next Step in Your IT Career?
We’re looking for a Junior Systems Administrator / MSP Technical Support Specialist to join a managed IT services team supporting business clients across a variety of technologies and environments.
This is an excellent opportunity for an IT professional with hands-on support experience who is ready to take greater ownership of technical issues, expand their Microsoft and MSP knowledge, and continue growing toward a Systems Administrator role.
You’ll work with Microsoft 365, Autotask, Kaseya/Datto, Windows, cloud technologies, networking, security tools, and more, while managing client issues from initial investigation through resolution or appropriate escalation.
If you’re technically curious, dependable, client-focused, and someone who takes ownership and makes sure issues don’t fall through the cracks, we’d like to hear from you.
What You’ll Be Doing
As part of the technical support team, you’ll be responsible for:
- Triaging, troubleshooting, and resolving technical support requests
- Taking ownership of assigned tickets and issues from initial investigation through resolution or appropriate escalation
- Managing tickets, documentation, and technical notes through Autotask Service Desk
- Using Kaseya/Datto RMM and related MSP tools for monitoring, management, and troubleshooting
- Providing support across the Microsoft ecosystem, including:
- Microsoft 365
- Exchange Online
- Outlook
- Teams
- SharePoint
- OneDrive
- Entra ID
- Intune
- Microsoft Defender
- Windows 10/11
- Troubleshooting workstations, applications, networking, VPNs, Wi-Fi, DNS, and other common IT issues
- Supporting desktop and laptop deployment
- Troubleshooting printers, scanners, monitors, peripherals, and basic hardware issues
- Following established escalation paths when additional expertise is required
- Providing complete and accurate technical information when escalating issues
- Communicating clearly and professionally with clients throughout the support process
- Maintaining accurate technical documentation and detailed ticket notes
- Identifying recurring issues and opportunities for proactive improvement
- Continuously developing your skills across Microsoft, cloud, security, networking, and MSP technologies
What We’re Looking ForRequired Qualifications
- Minimum 3 years of experience in IT support, service desk, or an MSP environment
- Working knowledge of Microsoft 365
- Strong Windows 10/11 troubleshooting experience
- Basic networking knowledge
- Understanding of Entra ID / Active Directory fundamentals
- Strong troubleshooting and problem-solving skills
- Ability to work within an MSP ticketing and escalation process
- Ability to prioritize and manage multiple tickets and responsibilities
- Strong communication and technical documentation skills
- Ability to work independently while recognizing when an issue needs to be escalated
- A genuine willingness to learn and continuously develop new technical skills
MSP Tools & Technologies
Experience with the following is preferred:
- Kaseya / Datto RMM
- Autotask PSA / Service Desk
- Remote monitoring and management tools
- Endpoint management and security tools
- Patch management
- Asset and client documentation systems
Experience with comparable MSP platforms will also be considered.
Additional Experience That Will Help You Stand Out
Experience or knowledge in any of the following areas would be considered an asset:
- Microsoft Intune
- Microsoft Defender
- Exchange Online
- SharePoint
- PowerShell
- Microsoft Azure
- Networking and firewalls
- DHCP, DNS, and Wi-Fi network troubleshooting
- Desktop and laptop deployment
- Printers and scanners
- Monitors and peripherals
- Basic hardware troubleshooting
- Backup technologies
- Cybersecurity technologies
- Microsoft certifications
Ownership Matters
One of the most important expectations of this position is ownership.
When an issue or ticket is assigned to you, you’ll be expected to:
- Investigate the issue thoroughly
- Work toward an effective solution
- Communicate with the client throughout the process
- Document your troubleshooting and work clearly
- Resolve the issue whenever possible
- Follow the appropriate escalation path when additional expertise is required
- Make sure the issue continues moving toward resolution
This role is about more than simply closing tickets. It’s about taking responsibility for client issues and making sure problems actually get resolved.
Grow Your Career
This position offers a clear technical career path:
Junior Administrator → Systems Administrator → Senior Systems Administrator
Progression is based on demonstrated technical competency, independence, ownership, and your ability to take on increasingly complex technologies and responsibilities.
As your skills develop, you’ll have opportunities to expand your knowledge across Microsoft technologies, cloud services, networking, security, MSP platforms, and business IT environments while working alongside experienced IT professionals.
What We Value
We’re looking for someone who is:
- Accountable: You take responsibility for your work and follow through on commitments.
- Curious: You want to understand why something happened, not simply apply a temporary fix.
- Organized: You can effectively manage tickets, documentation, priorities, and follow-ups.
- Client-focused: You understand that great technical support requires both technical ability and strong communication.
- Dependable: Clients and colleagues can count on you to follow through.
- Committed to learning: You’re motivated to continuously strengthen your technical skills and take on new challenges.
Working in an MSP environment is about more than closing tickets. It means taking ownership of client issues and becoming a trusted technical resource.
Why Apply?
- Build your career within a managed IT services environment
- Gain hands-on experience across a broad range of Microsoft and MSP technologies
- Work with Microsoft 365, Kaseya/Datto, Autotask, cloud, security, and networking technologies
- Work alongside experienced IT professionals
- Support a variety of business clients, environments, and technical challenges
- Continue developing your technical skills across multiple platforms
- Take on increasingly complex responsibilities as your knowledge and independence grow
- Follow a defined career path toward Systems Administrator and Senior Systems Administrator
How to Apply
Please submit your resume and briefly tell us about your experience with:
- Microsoft 365 and the Microsoft ecosystem
- Windows desktop support and troubleshooting
- MSP or service desk environments
- Autotask or comparable ticketing platforms
- Kaseya/Datto or other RMM tools
- Networking, cloud, security, or endpoint management technologies
If you’re an IT professional who enjoys troubleshooting, helping clients, taking ownership of technical issues, and continuously building your skills, we’d love to hear from you.
Pay: $20.00-$25.00 per hour
Work Location: Remote
