Team Lead, Technical Services

Johnston Group provides employee benefit solutions to over 30,000 companies, ranging from one employee to thousands across various product lines, including Chambers of Commerce Group Insurance Plan, Canada’s #1 employee benefits plan for small businesses. JG is a platinum member of Canada’s Best Managed Companies and was named one of Manitoba’s Top Employers. We support a positive work atmosphere where we value the diversity in the people we serve and are looking for talent who will contribute to our diverse and inclusive workplace; where individual differences are recognized, appreciated, and respected. JG believes in giving back and contributes significantly to local health, arts, sports, and other community organizations.

The Technical Services Team Lead is the senior technical authority for network and systems infrastructure and provides operational leadership for the Technical Services team. This role ensures smooth day-to-day IT support and acts as the primary escalation point for complex technical issues. This role serves as the technical point of contact for the team, facilitating cross-department collaboration and vendor communications. Team Lead, Technical Services drives continuous improvement by evaluating modern technologies, tracking SLAs, and staying ahead of emerging IT trends and threats, while mentoring team members to grow their technical depth. The goal is to enable an efficient, responsive support operation that meets or exceeds organizational service standards.

Key Responsibilities

• Lead and develop the Technical Services team through clear direction, coaching, and performance management (recruiting, onboarding, conflict resolution, engagement, and performance processes, career growth and goals)
• Oversee Technical Services project delivery by setting direction, approving priorities, and ensuring resourcing, governance, and outcomes from analysis through implementation and retrospectives
• Own portfolio prioritization by approving backlog priorities and aligning maintenance, operations, and project work to enterprise goals in coordination with team leads.
• Evaluate and oversee hardware, software, and infrastructure solutions, supporting procurement decisions (cost, fit, risk, and standards), inventory management, and refresh‑cycle coordination across the IT environment
• Provide strategic direction and oversight for IT infrastructure and platforms, including virtualization, physical infrastructure, lifecycle planning, vendor evaluation, network architecture, and data center or office hardware, while managing the IT Operations software‑licensing portfolio in accordance with signing‑authority guidelines
• Oversee enterprise infrastructure and system risk management by setting risk tolerance, prioritizing mitigation efforts, and reviewing outcomes to support business continuity

Qualifications

• Degree or diploma in Systems Administration or related program
• Must have basic knowledge of Project Management processes
• Minimum 5 years of experience in a Tier 2 technical support, Systems Administration, or Team Lead role
• Ability to communicate written and verbal information to both technical and non-technical audiences
• Ability to analyze problems and/or requirements and develop a suitable solution
• Advanced knowledge of enterprise networking, including LAN/WAN, VLANs, routing and switching (e.g., Cisco), firewalls (e.g., Palo Alto), VPN, DNS, and DHCP
• Advanced knowledge of systems administration, including Windows Server, Active Directory/Entra ID, Microsoft 365 (Exchange Online, SharePoint, Teams), group policy, and virtualization
• Ability to collaborate with employees with various business backgrounds and skill sets within the organization
• Ability to organize a number of projects and keep each on track
• Ability to work well in a team environment, particularly in a leadership role
• Have a proven track record of understanding the applications and business processes they support
• Have a proven track record of being able to investigate and resolve issues reported by users

The successful candidate must be legally eligible to work in Canada. We thank all applicants for their interest. Please note that only those selected for an interview will be contacted.

JG welcomes the opportunity to provide accommodation throughout the selection process. Please contact us to discuss your requirements by email at human.resources@johnstongroup.ca or by phone at 204-786-0421