Why this opportunity at Calligo?
Connect with colleagues globally
Working closely with colleagues across the UK, Europe and North America we have vibrant, modern office spaces all over the world!
Supportive and dynamic team
We know how hard our employees work and that our success comes from our people – a safe and supportive culture and employee wellbeing are at the heart of what we do.You’ll be joining our award-winning team and your primary responsibility will be managing the backup processes and associated tooling. This role blends deep technical expertise in endpoint and patch management, client infrastructure support, and on-site service delivery. You will ensure the performance, security, and compliance of client systems by leading endpoint lifecycle operations, implementing patch strategies, and supporting infrastructure across a variety of environments.
Interested?
The role would be well suited to an individual who has proven ability to show initiative and ownership of problems to conclusion. Also strong customer service orientation. Calligo Canada is an equal opportunity employer and we are committed to achieving greater accessibility by providing accommodation for people with disabilities during our hiring process. Accommodations are available on request for qualified candidates during each stage of the recruitment process.
Note: This role can work from the Oakville office on a hybrid basis with a minimum of one day per week spent in the office.
Endpoint & Patch Management
- Plan, deploy, and validate OS and third-party patches across client systems (Windows, macOS).
- Maintain endpoint compliance using Microsoft Intune, SCCM, JAMF, or RMM tools.
- Create and manage patch schedules, blackout windows, and emergency rollouts.
- Implement and enforce baseline security and configuration policies across endpoints.
Infrastructure & Systems Support
- Support client infrastructure including servers, network devices, and remote access tools
- Perform system imaging, software deployments, OS upgrades, and Group Policy management.
- Monitor and resolve alerts and tickets using PSA/RMM tools (e.g., Datto, ConnectWise).
- Provide Tier 2/3 support for escalated technical issues.
Client-Facing & On-Site Support
- Travel to client sites in GTA and surrounding areas for project delivery, installations, and escalated support.
- Build strong client relationships through professional, high-touch service.
- Provide technical walk-throughs, technology reviews, and user support sessions.
Operational Excellence
- Contribute to internal documentation and knowledge base articles.
- Identify and implement technical improvements and service enhancements.
- Ensure client systems adhere to cybersecurity, backup, and uptime requirements.
- 3–5 years of experience in a Systems Engineer, Endpoint Engineer, or similar role within a Managed Services environment.
- Strong knowledge of endpoint management tools (Microsoft Intune, SCCM, JAMF, PDQ Deploy, etc.).
- Solid understanding of Windows Server, Active Directory, Group Policy, DNS/DHCP, and file/print services.
- Hands-on experience with patch management, compliance reporting, and endpoint hardening.
- Proficiency in troubleshooting client environments both remotely and on-site.
- Scripting skills (PowerShell, Bash) for automation tasks are an asset.
- Excellent communication and time management skills.
Preferred Certifications
- Microsoft Certified: Endpoint Administrator Associate
- Microsoft Certified: Azure Administrator Associate
- CompTIA Security+ or Network+
- JAMF 100/200 or Apple Certified Support Professional
- ITIL v4 Foundations
- Training and development for career growth
- 25 Days Vacation, increasing with length of service
- RRSP matching
- Healthcare
- Life Insurance
- Flexible working
- Maternity & Parental top-up
- Paid volunteering time-off
