Senior Project Manager to lead a portfolio of IT initiatives and oversee multiple Project Managers to ensure projects are planned, governed, and delivered

12 Month Contract

3 days on site in Oshawa

Job Overview

• The Senior Project Manager (Contract) will lead a portfolio of IT initiatives and oversee multiple Project Managers to ensure projects are planned, governed, and delivered successfully.
• This role is highly hands-on: you’ll provide active coaching and “PM enablement” (as needed) to keep projects on track-removing blockers, strengthening execution, and ensuring consistent delivery practices across the program.
• You’ll manage complex workstreams such as application development, legacy application migrations to modern platforms, and data migration efforts.
• The ideal candidate is a well-rounded IT program leader who can work effectively across applications, data, and infrastructure teams-and who can manage budgets, forecasts, and resource plans with discipline.

Program & Portfolio Leadership

• Own end-to-end delivery for a portfolio of IT projects, ensuring alignment to business objectives, scope, schedule, and quality.
• Establish and maintain program governance: cadence, status reporting, RAID (Risks/Assumptions/Issues/Dependencies), decision logs, and executive updates.
• Drive cross-project dependency management and integrated planning across multiple teams and vendors.

Project Manager Leadership & Coaching

• Support Project Managers (contract and/or internal), setting expectations and ensuring consistent project controls.
• Provide hands-on guidance (“hand-holding” when needed) to strengthen PM execution-planning, stakeholder management, schedule discipline, and risk management.
• Standardize project delivery practices, templates, and reporting to improve predictability and transparency.

IT Delivery (Apps, Migration, Data)

• Lead programs involving: Application development / SDLC delivery (Agile, hybrid, or waterfall)
• Legacy application modernization and migration to new platforms/systems
• Data migration planning and execution (mapping, cleansing, validation, reconciliation, cutover)
• Partner with architecture, infrastructure, security, and operations to ensure environment readiness, performance, reliability, and supportability.
• Commissioning the project

Financial & Resource Management

• Build and manage program budgets, forecasts, and burn rates; track actuals vs. plan and drive corrective actions.
• Follow the Project Control Office direction and processes in managing the project financials
• Manage resource planning across workstreams (internal teams, contractors, vendors), including capacity, allocation, and onboarding/offboarding.
• Support procurement activities (e.g., SOW review, vendor coordination) as applicable.

Stakeholder & Executive Communication

• Serve as the primary point of contact for program health, timeline, risks, and decisions.
• Produce crisp, action-oriented updates for leadership; escalate issues with recommended options and impacts.
• Facilitate steering committees and key decision forums.

Qualifications

• 8+ years of progressive experience in IT project/program management, including leading multiple concurrent initiatives.
• Demonstrated experience managing Project Managers (directly or via dotted-line) and improving delivery execution through coaching and governance.
• Proven delivery experience in at least two of the following: Application development / systems implementation
• Legacy application migration/modernization
• Data migration (planning, execution, validation, cutover)
• Strong working knowledge of IT domains (applications, data, and at least foundational infrastructure concepts).
• Solid financial management experience: budgets, forecasts, vendor spend tracking, and resource planning.
• Excellent communication skills: executive-level status reporting, facilitation, and stakeholder management.
• Strong command of delivery fundamentals: schedules, critical path, RAID management, dependency mapping, change control.