About Us:

Constant C Technology Group is a leading Managed Service and Security Provider (MSSP) dedicated to helping our clients succeed by leveraging technology. We are a dynamic group of professionals committed to continuous learning, providing exceptional customer service, and fostering a supportive and collaborative team environment. We are looking for a senior technical expert to join our team and help drive client success through advanced solutions and mentorship.

Position Summary:

As a Senior IT Systems Administrator (Level 3), you are the final escalation point for all technical issues and a key player in designing and implementing robust IT solutions for our clients. You will be responsible for tackling the most complex technical challenges, leading projects, and mentoring our L1 and L2 technicians. This role requires a deep technical knowledge across networking, virtualization, cloud services, and security, combined with a strategic mindset and a passion for excellence.

Key Responsibilities:

• Handle all responsibilities of a Level 2 Technician and act as the primary escalation point for complex server, network, and application issues.
• Lead IT projects, including client onboarding, server migrations, network upgrades, and cloud deployments.
• Design, implement, and maintain advanced solutions involving Windows Server, Active Directory, Group Policy, and virtualization (Hyper-V/ESXi).
• Administer and troubleshoot complex networking environments, including advanced configuration of HP switches, Ruckus wireless, and firewalls (VLANs, routing, security policies).
• Manage and secure client cloud environments in Microsoft 365 and Azure, including advanced Entra ID and Exchange Online administration, and Conditional Access policies.
• Oversee and optimize backup and disaster recovery strategies using Veeam and Cove Backup.
• Provide expert-level support for VoIP systems (3CX) and respond to security incidents.
• Mentor and train L1/L2 technicians, fostering a culture of technical growth and knowledge sharing.
• Proactively identify opportunities for improvement in client environments and internal processes.

Required Skills & Qualifications:

• 5+ years of progressive experience in IT roles, with significant experience in a Systems Administrator or senior MSP technician role.
• Expert-level knowledge of Windows Server, Active Directory, Group Policy, and virtualization platforms (Hyper-V and VMware ESXi).
• Advanced networking skills, including routing, switching (HP), VLANs, and firewall management.
• In-depth experience with Microsoft 365 and Azure administration, including security and compliance features.
• Proven experience with backup and disaster recovery solutions (Veeam experience is highly desirable).
• Strong scripting and automation skills (e.g., PowerShell) to improve efficiency.
• A "Humble, Hungry, Smart" mindset: an expert who is always learning, a driver of solutions, and a natural leader and mentor.
• Ability to work full-time in our Winnipeg office (260-100 Innovation Drive).
• (Asset) Advanced industry certifications (e.g., MCSE, VCP, CCNA, Azure Administrator).
• (Asset) Valid Class 5 Manitoba Driver's License and access to a reliable vehicle.

What We Offer:

• A competitive salary and comprehensive benefits package (Health, Dental, Flex Days).
• A strong focus on professional development with support for high-level certifications and training.
• A leadership role within a highly collaborative team culture.
• The opportunity to design and implement cutting-edge solutions for a diverse client base.

If you are a senior IT professional ready to take on a challenging and rewarding leadership role, we encourage you to apply.