Senior Project Manager/Leader

Job Description Client: Land & Resources Cluster, Ministry of Public and Business Service Delivery and Procurement Location: Toronto, Ontario – 40 St. Clair West Assignment Term: August 24, 2026 – June 30, 2027 Work Arrangement: Hybrid – 3–4 days onsite / 1–2 days remote per week Hours: 7.25 hours/day, Monday–Friday, within standard hours of 8:00 AM–5:00 PM Openings: 1 Security Clearance: No clearance required Position Overview The Land & Resources Cluster is seeking a Senior Project Manager/Leader to provide project management leadership for a large-scale, highly complex, high-profile, multi-jurisdictional and enterprise-wide Discovery initiative aligned with the Ontario Digital Standard. The successful candidate will lead the project from inception through Discovery and subsequent project stages through implementation/go-live and close-out , ensuring effective management of scope, budget, schedule, risks, resources, stakeholders, governance, vendors and deliverables. The resource may also be assigned, as required, to projects or initiatives related to Bill 5 – Protect Ontario by Unleashing Our Economy Act 2025 . Key Responsibilities Provide senior project management leadership for large-scale, complex, high-profile, multi-disciplinary and enterprise-wide digital initiatives. Lead and oversee Discovery projects from inception through project close-out , including coordination of the Digital First Assessment (DFA) and transition to operations where required. Lead digital initiatives through progressive stages including Concept, Discovery, Design, Prototype, Implementation and Go-Live . Manage project scope, budget, schedule, resources, deliverables, financials, risks, issues, actions and decisions (IRAD) . Establish and manage project governance, including steering committees, gating reviews, checkpoints, reporting and escalation processes . Monitor project interdependencies, internal and external dependencies, risks, issues and exposure levels across multiple project streams. Lead stakeholder consultations, facilitation, consensus building and relationship management across business, IT, executive, vendor and external stakeholder groups. Build strong relationships with divisional stakeholders, subject matter experts, project teams, vendors and external parties. Develop and implement strategies to overcome resistance to change and capitalize on organizational forces supporting change. Provide strategic direction, recommendations, analysis and operational support to project teams and senior management. Translate business and IT executive expectations into clear project objectives, deliverables and outcomes. Lead and facilitate user research, service design, journey mapping, jurisdictional scans, conceptual solution development and problem-statement development . Coordinate and complete the Digital First Assessment (DFA) during the Discovery phase. Ensure project deliverables meet business requirements while adhering to approved scope, schedule, budget, quality and organizational standards. Develop and communicate project guidelines, procedures, status reports, dashboards, briefing materials, business cases, presentations and executive-level submissions. Work closely with senior leadership and executives and present project information and recommendations in a manner appropriate for executive audiences. Manage complex project issues and provide mitigation strategies and recommendations to senior decision-makers. Direct and coordinate multi-disciplinary project teams to ensure deliverables are completed on time and in accordance with government and ministry standards. Lead business transformation and change management activities associated with new solutions, systems and business processes. Support strategic IT investment planning and business case development for new system implementations and enhancements. Develop procurement artifacts, including RFS, RFP/SOW, contracts and approval documentation , in accordance with applicable organizational policies. Manage Discovery vendors and vendor deliverables, providing effective oversight and vendor management throughout the project lifecycle. Lead vendor teams through planning, milestones, guidance, policies, procedures and deliverables. Influence vendor teams to deliver on-scope, on-time, on-budget and high-quality outcomes that are properly integrated with client deliverables. Apply Agile and OPS Digital approaches , project management methodologies, standards, guidelines and best practices. Requirements Mandatory Qualifications & Experience Senior Project Management 10+ years of senior project management experience. Demonstrated experience leading large, complex, high-profile, multi-disciplinary projects involving multiple business and IT stakeholders. Strong experience managing scope, budget, schedule, risks, issues, actions, decisions, resources, deliverables and governance . Proven experience leading digital initiatives through Concept, Discovery, Design, Prototype, Implementation and Go-Live . Proven experience leading and overseeing Discovery initiatives from inception through close-out . Experience with project governance committees, including steering committees, gating reviews and checkpoints . Experience managing project financials, resources, reporting and escalation. Discovery, Digital & Transformation Experience coordinating Digital First Assessments (DFA) . Experience leading user research, service design, journey mapping, jurisdictional scans and conceptual solution development. Experience developing and articulating problem statements and translating business needs into project deliverables. Experience leading business transformation and change management initiatives. Proven ability to develop and implement strategies to overcome resistance to change. Experience supporting business planning, benefits identification and organizational funding requests for I&IT initiatives. Experience supporting strategic IT investment planning and business case development. Stakeholder & Executive Engagement Proven experience leading stakeholder consultations, facilitation and consensus building . Strong political acuity and ability to collaborate, share information and build relationships across multi-disciplinary stakeholder groups. Ability to establish and facilitate effective IT partnerships with business clients. Demonstrated ability to understand business directions, objectives and priorities and translate them into project outcomes. Strong facilitation, negotiation, diplomacy and conflict-resolution skills. Experience managing stakeholder expectations and obtaining buy-in from senior management and key stakeholders. Proven experience building strong relationships with senior leadership and executive stakeholders. Experience producing and presenting executive-level presentations, dashboards, briefing papers, submissions, business cases and status reports . Vendor & Procurement Management Experience managing vendor teams through project planning, milestones, policies, procedures, guidance and deliverables. Demonstrated ability to influence vendors to achieve on-scope, on-time, on-budget and quality deliverables . Experience managing vendor deliverables and integrating vendor outputs with client deliverables. Experience developing procurement artifacts, including RFS, RFP, SOW/Contract and approval documentation . Knowledge of procurement processes and organizational policies for acquiring services, vendors, business solutions and project resources. Project Team Leadership Experience directing, managing and leading multi-disciplinary project teams . Extensive experience coordinating project processes, interactions, progress, roadblocks and dependencies. Ability to establish and communicate project guidelines, procedures and standards. Demonstrated ability to provide strategic direction and operational support to project teams and stakeholders. Experience monitoring technical and business performance of complex projects. Public Sector / Government Experience leading large, complex, multi-disciplinary Discovery and IT/business projects within municipal, provincial or federal government environments . Experience working within public-sector governance, project management methodologies and organizational standards. Experience leading or coordinating Digital First Assessment, Cyber Security, Privacy, Architecture and Project Gating activities for public-sector projects. Project Management Certification Formal project management training or certification such as PMP, Scrum and/or Agile . Evaluation Criteria 1. Project Management Experience – 30% Candidates will be assessed on: Large, complex and high-profile multi-disciplinary project leadership. Strong scope, budget, schedule and IRAD management. Digital initiatives spanning Concept, Discovery, Design, Prototype, Implementation and Go-Live. Discovery project leadership from inception through close-out. Governance committees, financials, resources, reporting and escalation. Stakeholder consultation, facilitation and consensus building. Senior leadership engagement and executive-level presentations/products. Transformation and change management leadership. PMP, Scrum, Agile or equivalent formal project management training/certification. 2. Leadership & Communication – 20% Political acuity and relationship-building capabilities. Ability to establish strong business/IT partnerships. Executive-level communication and presentation skills. Experience producing presentations, dashboards, briefing papers, submissions, business cases and status reports. Senior leadership and executive relationship management. Business transformation and change management experience. Strategic IT investment planning and business case support. 3. Stakeholder Engagement & Relationship Building – 25% Strong facilitation, negotiation and diplomacy. Ability to resolve issues, defuse tensions and achieve stakeholder buy-in. Strong understanding of business processes and requirements. Ability to manage stakeholder expectations and establish clear project scope and requirements. Experience working collaboratively with vendors and internal/external stakeholders. Ability to influence senior management and client leadership. 4. Procurement & Vendor Management – 20% Procurement knowledge and experience developing RFS/RFP/SOW/Contract artifacts. Vendor team leadership and management. Experience managing vendor milestones, deliverables, policies and procedures. Ability to influence vendors to deliver quality outcomes within scope, schedule and budget . Experience integrating vendor deliverables with client deliverables. 5. Public Sector Experience – 5% Government experience at the municipal, provincial or federal level . Experience leading complex Discovery and IT/business projects in a public-sector environment. Experience with Digital First Assessment, Cyber Security, Privacy, Architecture and Project Gating . Desirable Skills Knowledge of OPS enterprise architecture practices , particularly business and information architecture. Knowledge of Information Management principles, concepts, policies and practices . Experience applying both predictive and Agile methodologies . Knowledge of the Accessibility for Ontarians with Disabilities Act (AODA) and related regulations and standards. Previous Ontario Public Service (OPS) experience is strongly preferred. Ideal Candidate Profile The ideal candidate is a Senior Project Manager/Leader with 10+ years of experience managing complex digital and IT transformation initiatives, preferably within a public-sector environment. The candidate should demonstrate a strong combination of: Enterprise-scale project leadership Discovery and digital transformation experience Executive and senior stakeholder engagement Strong political acuity and diplomacy Agile/OPS project management knowledge Vendor and procurement management Change management and transformation leadership Strong governance, risk and financial management Excellent executive communication and presentation skills Government/public-sector project experience Work Arrangement: Hybrid, with 3–4 days per week onsite at 40 St. Clair West, Toronto , and 1–2 days remote. Candidates must be comfortable meeting this onsite requirement. Upstaff is an Equal Opportunity Employer and does not discriminate on the basis of race or ethnicity, religion, sex, national origin, age, veteran disability or genetic information or any other reason prohibited by law in employment.