Job Number: 53152
We’re seeking a Systems Support Services Lead to drive the strategic direction and optimal use of the City’s purchasing system. Reporting to the Manager of Systems Processing & Support Services, you’ll provide expert guidance to over 2,000 internal users and 3,500 suppliers.
This role is for a proactive leader who can translate strategic goals into actionable initiatives, using data to identify trends and implement solutions. You will be instrumental in developing policies, leading training, and ensuring compliance across a system that handles over $2B in annual spending. If you’re passionate about leading teams and leveraging technology to maximize efficiency and mitigate risk, we encourage you to apply.

SKILLS REQUIRED FOR SUCCESS:

• Strong knowledge of public sector procurement, contract management, and tendering laws, including trade agreements.
• The ability to align daily system operations with broader organizational goals and contribute to strategic frameworks.
• Proven skills in leading, coaching, and empowering teams to achieve key initiatives.
• Expertise in using data analytics and visualization to interpret system performance and present actionable insights.
• Experience with process re-engineering methodologies like Lean or Six Sigma to drive efficiency
• Demonstrated ability to manage the people-side of change, ensuring successful adoption of new initiatives
• Exceptional verbal and written communication skills to persuade and build consensus among diverse partners, including executive leadership
• Capacity to evaluate and recommend new technologies and industry trends to enhance system capabilities
• Strong skills in resolving complex issues and negotiating with groups that have competing interests
• Proven ability to manage program delivery using project management principles and tools

Qualifications:

• Bachelor’s Degree in Business Administration, Public Administration or a related discipline, or equivalent is required
• A minimum of five (4) years of progressively responsible experience within a large, complex unionized organization, preferably within the public sector. Two (2) or more years of progressively responsible supervisory experienc

• Working in collaboration with the Manager, Systems Processing & Support Services for leadership duties of Systems Processing staff reporting to the position including but not limited to hiring, work assignments, delegation, and performance management/documentation
• Lead the strategic development of a highly skilled and adaptive Systems Support Services team, anticipating future system and user needs and implementing proactive talent development and succession planning initiatives
• Accountable to ensure the team is aware of the areas of staff and supplier knowledge gaps and work with them on corrective actions such as updates to training
• Regularly meet as a team and individually to monitor staff’s workload, engagement, and performance and implement corrective actions plans as necessary
• Provide leadership, development, coaching, performance evaluation, and feedback to staff while proactively communicating and escalating to the Manager, Systems Processing & Support Services where needed
• Lead the design and delivery of advanced, data-driven training curricula for staff and key internal/external partners, ensuring comprehensive understanding and optimal utilization of system capabilities and new functionalities, thereby influencing best practices across the organization
• Provide reporting on teams performance measures against targets set by the Manager, Systems Processing & Support Services
• Develop and implement sophisticated analytical models and dashboards to monitor system adoption, user proficiency, supplier engagement, and compliance trends, providing actionable insights for strategic intervention and continuous improvement
• Ensure team’s effectiveness through measurement against key performance indicators
• Lead the design and implementation of advanced quality assurance frameworks for system support and supplier enablement, leveraging lessons learned and data analytics to drive systemic improvements and mitigate risks
• Proactively complete and participate in analysis and research of the broader market research, industry trends, patterns and recurrences to ensure the City is utilizing best practises
• Lead the strategic integration of industry best practices and emerging technologies into the City’s systems support framework, ensuring the continuous evolution and competitiveness of procurement and contract management functions
• Work in conjunction with Technology and Integration team to implement system updates
• Lead cross-functional initiatives with Technology and Integration to define system requirements, evaluate new solutions, and manage the implementation of major system enhancements, serving as a key business lead for technical projects impacting contract and purchasing systems
• Other related responsibilities

Qualifications:

• Bachelor’s Degree in Business Administration, Public Administration or a related discipline, or equivalent is required
• A minimum of five (4) years of progressively responsible experience within a large, complex unionized organization, preferably within the public sector. Two (2) or more years of progressively responsible supervisory experience