Senior Systems Administrator at STACK IT… · Toronto

Build, Optimize, and Elevate the Modern Workplace as a Senior Systems Engineer!

Our client is seeking a Systems Engineer to support and enhance the technologies that underpin its day-to-day operations. This is an exciting opportunity to contribute to a forward-thinking IT function, where innovation, automation, and continuous improvement are viewed as essential components of success.

In this role, you'll lead initiatives across Microsoft 365, endpoint management, and identity services, while partnering with stakeholders to deliver reliable, secure, and user-focused technology solutions. If you enjoy identifying smarter ways of working and taking ownership of meaningful technical initiatives, this role offers both challenge and influence.

💻 Who You Are:

• You're the person people call when systems need more than a quick fix.
• You thrive in environments where you can own critical technology platforms, simplify complexity, and build solutions that make life easier for everyone around you. You're equally comfortable diving deep into Microsoft 365 architecture, automating repetitive processes, and supporting executives when the stakes are high.
• You believe great IT isn't just about keeping systems running, it's about creating secure, scalable experiences that allow businesses to move faster.
• You're naturally curious, solutions-oriented, and always asking, "How can we do this better?"

📍 Work Type

• Location: Toronto, ON (Fully On-site – 5 days a week in office)
• Vacancy Type: This role is a newly created position

🎯 What You'll Do:

• Take ownership of the day-to-day administration, optimization, and continuous improvement of Microsoft 365 services, including Exchange Online, SharePoint, Teams, and OneDrive.
• Manage and enhance Entra ID environments by supporting identity lifecycle processes, Conditional Access policies, role-based access controls, and authentication best practices.
• Administer Microsoft Intune across Windows and macOS environments, ensuring devices remain secure, compliant, and efficiently managed throughout their lifecycle.
• Design, implement, and maintain automation solutions that streamline repetitive IT processes, including onboarding, offboarding, provisioning, and license management.
• Develop and maintain scripts and workflows using PowerShell and other automation tools to improve operational efficiency and reduce manual effort.
• Act as a senior escalation point for complex technical issues involving identity, endpoint management, and Microsoft technologies, driving issues through to resolution.
• Provide exceptional support to executive stakeholders, delivering a high level of professionalism and discretion in time-sensitive situations.
• Collaborate with internal teams to strengthen security practices, support business continuity initiatives, and ensure technology solutions align with organizational needs.
• Contribute to the development and management of the IT budget, including forecasting technology needs, overseeing software and hardware renewals, evaluating vendor proposals, and identifying cost-effective solutions that support business objectives
• Create and maintain technical documentation, runbooks, and standard operating procedures to support knowledge sharing and operational consistency.
• Continuously evaluate existing processes and technologies, identifying opportunities to improve the employee experience, enhance security, and modernize the IT environment.

⭐ What We're Looking For (Our Wishlist):

• 6+ years of experience in systems administration, systems engineering, endpoint engineering, or a related role.
• Strong hands-on expertise with Microsoft 365 administration.
• Deep understanding of Entra ID, Conditional Access, MFA, and identity best practices.
• Proven experience managing Microsoft Intune environments.
• Advanced PowerShell skills, with experience in automation and scripting.
• Exposure to Python, Power Automate, or similar automation technologies.
• Solid understanding of networking fundamentals, including DNS, DHCP, TCP/IP, VPN technologies, and security principles.
• Experience supporting senior stakeholders in fast-paced environments.
• Exceptional troubleshooting, communication, and documentation skills.
• Ability to work independently while collaborating effectively across teams.

Nice to Have:

• Microsoft certifications such as MS-102, AZ-104, SC-300, MD-102, or equivalent.
• Exposure to Azure Functions, Logic Apps, or automation within Azure environments.
• Experience supporting multi-tenant Microsoft environments.
• Familiarity with AI-enabled productivity solutions and workflow enhancements.
• Background working within financial services, professional services, or similarly fast-moving industries.

🔥 What Makes This Role Exciting?

• Meaningful Ownership: You'll have the opportunity to influence how core business technologies are managed and improved.

• Automation with Purpose: If you've ever thought, "There has to be a better way," you'll have the freedom to build it.

• Variety Without Chaos: One day you might be enhancing endpoint management processes; the next, you're working on identity improvements or tackling a complex escalation.

• Collaboration & Impact: You'll work alongside talented professionals who value initiative, thoughtful problem-solving, and continuous improvement.

• Salary: $110,000 - $125,000

• Comprehensive Benefits Package & Paid Time Off

📩 Ready to Grow Your IT Career? Apply Now!

At STACK IT Recruitment, we connect technical talent with meaningful opportunities across Canada. If you meet around 70% of the qualifications, we encourage you to apply — we’d love to chat.

Know someone who’d be a great fit? Share this posting and help them take the next step in their IT career.

✨ We’re proud to support diversity and inclusion. If you require accommodation during the hiring process, just let us know — we’re happy to help.

AI Use Disclosure:

STACK IT uses AI-enhanced tools to support initial candidate screening and interview note analysis. All assessments and hiring decisions remain human-led.