Senior Project Manager to lead portfolio of IT initiatives and oversee Project Managers to ensure projects Job Toronto area,Ontario

Position: Senior Project Manager to lead a portfolio of IT initiatives and oversee multiple Project Managers to ensure projects

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.