Project Manager/Leader - Senior
Upstaff
Senior I&IT Project Manager
Location: Ontario (Onsite)
Work Arrangement: Full-time Contract – 5 Days Onsite
Contract Type: Contract
Job Overview
We are seeking an experienced Senior I&IT Project Manager to lead the discovery and planning phase of a major enterprise modernization initiative spanning multiple Ontario government ministries. The successful candidate will coordinate cross-ministry governance, strategic planning, stakeholder engagement, risk management, executive reporting, and project delivery activities while ensuring alignment across business and technology workstreams.
This role requires a seasoned project management professional with experience leading large-scale public sector initiatives, supporting executive governance, and delivering projects using Ontario Public Service (OPS) project management methodologies.
Key Responsibilities
- Provide senior project management leadership throughout the complete project lifecycle, from initiation through project close-out.
- Coordinate cross-ministry governance activities and ensure alignment between business partners, I&IT teams, and executive leadership.
- Develop, maintain, and monitor comprehensive project plans, schedules, milestones, dependencies, budgets, and critical path activities.
- Manage project scope, risks, issues, assumptions, decisions, and change requests while ensuring timely resolution of project challenges.
- Prepare executive-level project status reports, dashboards, presentations, and briefing materials for senior management.
- Lead and facilitate Executive Steering Committee, Director, Working Group, and stakeholder meetings, including agenda preparation, meeting minutes, and action item tracking.
- Support Treasury Board (TB), Management Board of Cabinet (MBC), and Strategic Planning Process (SPP) submissions by coordinating required documentation and approvals.
- Coordinate procurement activities, including future Request for Bid (RFB) planning and vendor engagement support.
- Manage project governance submissions and reporting through Planview while ensuring compliance with OPS Project Portfolio Management (PPM) standards.
- Apply and support the Ontario Public Service Unified Project Management (UPM) methodology throughout all project phases.
- Coordinate project governance artifacts, ensuring compliance with organizational standards and quality requirements.
- Support change management planning, stakeholder readiness, organizational adoption, and business transition activities.
- Collaborate with business and technical teams to ensure successful delivery of modernization initiatives.
- Monitor financials, project performance, deliverables, and resource utilization throughout the project lifecycle.
- Support post-implementation reviews, lessons learned sessions, and project close-out activities.
Required Qualifications
- Minimum 5 years of senior Project Management experience leading large-scale enterprise I&IT projects.
- Proven experience managing complex projects across multiple business and technology stakeholders.
- Experience supporting Treasury Board (TB) , Management Board of Cabinet (MBC) , and Strategic Planning Process (SPP) submissions.
- Strong knowledge of project governance, executive reporting, and portfolio management practices.
- Experience managing project schedules, milestones, budgets, risks, issues, and key deliverables.
- Experience coordinating procurement activities and supporting RFB planning.
- Strong experience preparing executive presentations, reports, dashboards, and briefing materials.
- Experience using Planview for project governance, portfolio management, and project tracking.
- Strong knowledge of the Ontario Public Service Unified Project Management (UPM) methodology and gateway process.
- Demonstrated experience leading cross-functional teams and facilitating executive governance meetings.
- Excellent communication, presentation, negotiation, and stakeholder management skills.
- Strong analytical, organizational, and problem-solving abilities.
- Experience leading organizational change management initiatives.
- Knowledge of business applications related to annual funding allocation processes is considered a strong asset.
Technical & Project Management Skills
- Enterprise Project Management
- Project Planning & Scheduling
- Risk & Issue Management
- Budget & Financial Management
- Scope & Change Management
- Executive Reporting
- Stakeholder Management
- Governance & Compliance
- Portfolio Management
- Planview PPM
- Ontario Public Service UPM Methodology
- Project Lifecycle Management
- Procurement Coordination
- RFB Planning
- TB/MBC Submission Support
- Strategic Planning Process (SPP)
- Executive Steering Committee Management
- Organizational Change Management
- Resource Planning
- Vendor Management
- Quality Assurance
- Project Documentation
- Project Governance
- Business Case Development
- Meeting Facilitation
- Status Reporting
Preferred Qualifications
- Previous experience working within the Ontario Public Service (OPS) or a comparable public sector organization.
- Experience delivering enterprise modernization and digital transformation initiatives.
- Knowledge of GO-ITS standards and Ontario government architecture and governance practices.
- Understanding of funding allocation systems and ministry data challenges.
- Experience working within complex, multi-ministry environments.
- PMP certification or equivalent project management certification is considered an asset.
Preferred Technologies & Methodologies
- Planview
- Microsoft Project
- Microsoft Office Suite
- SharePoint
- Azure DevOps (Asset)
- OPS Unified Project Management (UPM)
- Project Portfolio Management (PPM)
- ITIL (Asset)
- Agile
- Waterfall
- Hybrid Project Delivery
- Change Management Methodologies (Prosci/ADKAR preferred)
Preferred Industry Experience
- Ontario Public Service (OPS)
- Government of Ontario
- Public Sector Digital Transformation
- Enterprise I&IT Modernization
- Cross-Ministry Programs
- Large Enterprise Project Delivery
- Public Sector Governance & Portfolio Management
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