Senior Project Manager, Transportation

The Transportation Roadmap focuses on implementing and enhancing critical systems that support vehicle scheduling and dispatch, operator scheduling, and customer interaction. This includes the Reservation, Scheduling, and Dispatch system used by customers and staff to book trips, schedule vehicles, and support dispatch operations.

The role also supports the implementation of a digital Yard Management platform that provides near real-time visibility into the bus fleet, including eBus charge levels, range, location, and charging infrastructure. The solution will enable dispatchers to manage fleet operations by garage and shift, supported by integrated dispatch logic, configurable business rules, and automated operator notifications. The initiative aims to improve operational efficiency, service reliability, and long-term sustainability.

The incumbent will manage all phases of the project life cycle, ensuring delivery of scope, schedule, and performance objectives within approved budgets. Responsibilities include developing and executing detailed project plans, schedules, budgets, and communication plans, as well as overseeing day-to-day project execution.

This role requires a seasoned Project Manager with strong leadership, facilitation, and communication skills, capable of managing diverse teams across technology, business, operations, and vendor groups. The incumbent is responsible for clearly communicating program vision, maintaining stakeholder alignment, and ensuring successful delivery of all ITS components of the program.

This is a part-time position, typically requiring two days per week, with flexibility to increase to up to 35 hours per week as needed.

• Mandatory Skills

• Must hold current Project Management Professional (PMP) certification from PMI
• 15+ years’ experience in managing technology components of major transportation projects.
• Post-secondary education in the related discipline.

• Other Skills

• Proven delivery of at least five multi-year, highly complex, cross-functional initiatives
• Demonstrated experience managing cross-functional projects involving technology teams, business stakeholders, and large vendors with established relationships
• Proven ability to plan and deliver projects in accordance with approved schedules, project plans, funding processes, and staffing requirements
• Experience managing multi-phased projects and leading diverse teams within a functional matrix environment
• Comprehensive knowledge of project management principles and practices, including work scheduling and resource allocation
• Advanced proficiency with MS Project/POL, including development and maintenance of detailed project schedules
• Experience managing multiple vendors concurrently
• Fifteen or more years of progressively responsible IT experience, with a strong focus on business problem-solving
• Experience using SharePoint as a document repository and proficiency with the MS Office Suite
• Sound knowledge of business administration, financial management, human resources policies, and applicable legislation and regulations (e.g., safety, human rights, employment)
• Demonstrated ability to manage multidisciplinary teams, resolve complex issues, and maintain effective working relationships
• Knowledge of, or ability to rapidly acquire knowledge of, the Ontario Human Rights Code and related orders, including disability accommodation and accessibility requirements for passengers and employees
• Excellent written and verbal communication skills

• Lead end-to-end project management activities, including scope, schedule, budget, resourcing, and communications
• Manage and deliver all project artifacts in accordance with the ITS Project Management Framework
• Develop and maintain project plans, schedules, WBS, resource plans, and cost management plans, including bottom-up estimates
• Provide regular and ad-hoc project status, performance, budget, and risk reporting
• Support the Director with financial forecasting, actuals tracking, and resource allocation
• Conduct risk and issue management, including assessments, mitigation strategies, and reporting
• Plan, schedule, and manage project deliverables, milestones, and gating activities
• Provide leadership and direction to cross-functional project teams, consultants, and vendors
• Coordinate staffing, work plans, and resource assignments across project phases
• Implement project communication and stakeholder engagement plans
• Support production operations, system issues, and user training during rollout
• Ensure data accuracy, quality, and integrity across all project documentation
• Complete project closeout activities and required documentation
• Collaborate with ITS PMO and participate in governance, portfolio reviews, and budget processes

• Governance, project initiation, and lifecycle documentation
• Procurement support in accordance with ITS approvals and guidelines
• Stakeholder engagement and project communications deliverables
• Day-to-day management and oversight of project scope, schedule, budget, resourcing, and communications
• Project plans and artifacts in alignment with the ITS Project Management Framework, including schedules, status reports, and risk/issue logs
• Development and maintenance of WBS, resource plans, project management plans, and cost management plans (including bottom-up estimates)
• Regular and ad-hoc project, performance, risk, and budget reporting, including Steering Committee materials
• Financial reporting support to the Director, Project Management (planned vs. actuals, forecasting, time-based costing, and resource allocation)
• Change management deliverables supporting digital transformation
• Project closeout documentation and other required project records