Job Summary
The IT Team Leader is responsible for the overall leadership, coordination, and continuous improvement of DARTS’ information technology systems, applications, and planning infrastructure. This role ensures that technology solutions support organizational strategy, operational efficiency, and service delivery.
Reporting to the Operations Manager, the IT Team Leader provides direction, oversight, and support to the Applications Developer and Planning & Deployment Coordinator. The role integrates application development, transit scheduling systems, and IT infrastructure to ensure cohesive, reliable, and scalable technology operations.
The IT Team Leader works cross-functionally with internal departments and external IT partners to plan, prioritize, and implement technology initiatives, while fostering a culture of innovation, accountability, and continuous learning. The role is also accountable for ensuring business continuity through effective contingency planning.
The IT Team Leader holds end-to-end accountabilities for all organizational information technology, including enterprise applications, infrastructure, end-user computing, networking, cybersecurity, data protection, and IT governance. This role supports and aligns efforts to ensure the reliability, security, and compliance of all IT services supporting DARTS operations.
Responsibilities
Leadership & Team Management
- Provide day-to-day leadership, guidance, and performance management to the Applications Developer and Planning & Deployment Coordinator.
- Establish clear priorities, goals, and deliverables aligned with organizational strategy.
- Support employee development through coaching, training, and performance feedback.
- Foster collaboration between technical and operational functions.
Technology Strategy & Planning
- Translate organizational goals into IT operational plans and initiatives.
- Identify opportunities to enhance systems, applications, and processes to improve service delivery.
- Lead planning for system upgrades, integrations, and new technology implementations.
- Ensure alignment between application development, scheduling systems, and operational needs.
Systems & Application Oversight
- Oversee the development, maintenance, and optimization of DARTS’ applications and systems.
- Ensure reliability and performance of mission-critical systems, including Trapeze and Call Centre platforms.
- Promote systems thinking to ensure seamless integration across departments.
- Ensure appropriate documentation, testing, and lifecycle management of systems.
Business Continuity & IT Operations
- Develop, implement, and maintain IT contingency and business continuity plans to ensure uninterrupted service delivery.
- Lead preparedness and response for system outages, power failures, and other operational disruptions.
- Ensure internal maintenance of DARTS’ IT systems, including proactive monitoring, updates, and lifecycle management.
- Coordinate backup systems, redundancy measures, and disaster recovery processes.
- Conduct regular testing of contingency plans and update procedures based on lessons learned.
- Ensure critical systems supporting Call Centre, scheduling, and operations remain functional during disruptions.
Operational Support & Continuous Improvement
- Monitor system performance and identify opportunities for efficiency and improvement.
- Lead process design and re-engineering initiatives across IT and scheduling functions.
- Ensure technology supports effective service planning, scheduling, and deployment.
- Promote adoption of best practices, innovation, and continuous improvement.
Stakeholder & Vendor Management
- Act as the primary liaison with external IT vendors and service providers.
- Collaborate with internal stakeholders to understand and respond to technology needs.
- Ensure effective communication between IT and operational teams.
Compliance & Risk Management
- Ensure compliance with organizational policies, cybersecurity practices, and applicable legislation.
- Support data security, system integrity, and risk mitigation strategies.
- Maintain awareness of emerging risks and implement appropriate safeguards.
IT Asset & Inventory Management
- Develop and maintain a centralized inventory system for all DARTS IT equipment (e.g., monitors, docking stations, laptops, peripherals).
- Establish and manage processes for requesting, approving, issuing, tracking, and replacing IT equipment.
- Maintain accurate asset records, including assignment, location, and lifecycle status.
- Monitor inventory levels and coordinate procurement to meet operational needs.
- Ensure secure handling, reallocation, and disposal of IT assets in accordance with organizational policies.
Other
- Maintain compliance with health and safety policies.
- Perform other duties as required.
Job Specifications
Education & Experience
- Post-secondary education in Information Technology, Computer Science, Information Systems, or a related field. An equivalent combination of education and relevant IT experience will be considered.
- Minimum 3–5 years of experience in IT systems, application development, or technology operations.
Technical & Functional Skills
- Windows Server (Active Directory, Group Policy, DNS, DHCP)
- Microsoft 365 / Azure AD (user management, licensing, security policies)
- Endpoint management (Intune or similar)
- Backup & recovery solutions
- Automation mindset (PowerShell, basic scripting)
- Strong understanding of application development, database systems, and IT infrastructure.
- Experience with Microsoft environments, SQL databases, and enterprise systems.
- Familiarity with transit scheduling systems (e.g., Trapeze) is an asset.
- Knowledge of cybersecurity principles and best practices.
Networking
- Solid understanding of:
- TCP/IP, VLANs, subnetting.
- Firewalls, VPNs.
- Switches/routers (Cisco, Ubiquiti, etc.).
Hardware & Infrastructure
- Servers (on-prem or hybrid).
Core Skills/Experience
- Strong leadership, decision-making, and problem-solving abilities.
- Strong organizational and prioritization skills in a dynamic environment.
- Previous leadership experience is preferred.
- Experience in a unionized environment is an asset.
- Experience in a Call Centre, Transit/Logistics, and/or 24/7 operation environments is an asset.
Nice-to-Have Certifications
- CompTIA Network+ / Security+.
- Microsoft (Azure, M365, Windows Server).
- Cisco (CCNA).
Pay: $80,000.00-$90,000.00 per year
Benefits:
- Company events
- Company pension
- Dental care
- Disability insurance
- Employee assistance program
- Life insurance
- On-site parking
- Vision care
- Wellness program
Application question(s):
- This is an in-person position. Are you local to Hamilton, Ontario (within 1 hour commute)?
Work Location: In person
