We’re growing! We're looking for passionate, driven and energetic candidates to join our Technology Solutions team for the position of Senior System Administrator located in our Head Office in Guelph, Ontario.

Compensation: Starting at $75,000 annually plus bonus.

Are you passionate about managing a broad range of IT related tasks and projects to reach a shared goal of profitable operation through increased efficiency? As a Senior System Administrator, you will maintain and enhance Skyline’s technology infrastructure, proactively investigate and resolve advanced technical issues, and provide strategic recommendations to improve the company’s IT systems. You will design, implement, and support secure, scalable solutions across on-premises and cloud platforms, with a strong focus on Azure and enterprise networking. In this role, you will act as a senior escalation point, lead infrastructure projects, and collaborate with stakeholders, vendors, and IT teams to deliver reliable, high-performing systems that support Skyline’s goal of creating meaningful value and an exceptional experience for our customers, our people, and our communities.

What you will be doing:

• Design, implement, and maintain enterprise infrastructure across Windows, Linux, virtualization, and hybrid cloud environments supporting regional offices, remote locations and ventures.
• Lead the deployment, management, and optimization of Azure-based solutions including virtual machines, networking, storage, and hybrid connectivity.
• Administer Microsoft 365 services including Exchange Online, SharePoint, OneDrive, Teams, and identity/access management.
• Act as a senior escalation point for complex infrastructure, cloud, and networking issues, providing advanced troubleshooting and root cause analysis.
• Design, configure, and troubleshoot enterprise TCP/IP networking including routing, switching, VLANs, firewalls, VPNs, and wireless infrastructure.
• Architect and support Azure networking including VNETs, subnets, routing, and hybrid connectivity (VPN, ExpressRoute).
• Implement and maintain system patching, backup, and disaster recovery processes to ensure platform reliability and security.
• Develop and maintain standard operating procedures (SOPs) and technical documentation.
• Provide mentorship and technical guidance to System Administrators and Service Desk staff.

• Expertise in Microsoft technologies including Windows Server, Active Directory (hybrid), and Microsoft 365.
• Strong hands-on experience designing, implementing, and supporting Microsoft Azure infrastructure and hybrid cloud environments.
• Advanced networking expertise in TCP/IP, routing, switching, VLANs, firewalls, DNS, and DHCP across both on-prem and cloud environments.
• Experience with ITIL processes including Incident, Change, and Asset Management.
• Proven ability to design and support highly available, scalable, and resilient infrastructure solutions.
• Strong troubleshooting and analytical skills with experience handling complex enterprise-level issues.
• Patience, patience, patience!  And a sense of humour that goes a long way to make our internal customers feel more comfortable with technology.
• Experience with servers, virtualization platforms, storage solutions, and backup/disaster recovery strategies.
• Excellent documentation discipline with experience maintaining SOPs and technical standards.
• Strong communication and leadership skills with the ability to mentor team members and work cross-functionally.
• Minimum 7 years of relevant infrastructure experience with post-secondary education in IT or equivalent combination of experience.

• You like to be recognized for the magic you do.
• Providing great customer service is something you thrive on.
• You get a thrill from staying organized and details are your “thing”.
• Being part of a great team has been your dream.
• You see the matrix (i.e. have good judgement and innovation).
• Working for a growing company that supports environmental stewardship and social responsibilities is a must for you.
• You want to work for a company that supports work-life balance and truly cares that you are 100% fulfilled in your life.

Why Skyline?

Skyline is a capital management company that acquires, develops, and manages real estate properties and clean energy assets, and offers them as private alternative investment products.

We offer our employees competitive pay, benefits, time-off for volunteering opportunities, on-going training, growth potential and so much more! Our workplace culture empowers staff at all levels to become involved in supporting and building vibrant communities. 

We are an equal opportunity employer committed to diversity and accessibility. Accommodations are available upon request by contacting Skyline Human Resources at [email protected].