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Massey Henry is pleased to once again support the Ontario Securities Commission (“OSC”) — this time in the recruitment for a Head of the Strategic Project Management Office (“Head”).
 
About the Ontario Securities Commission Organization
 
The Ontario Securities Commission (“OSC”) is an independent Crown agency that regulates Ontario’s capital markets by making rules that have the force of law and by adopting policies that influence the behaviour of capital markets participants.
 
The OSC carries out the powers, duties and functions given to it pursuant to the Securities Commission Act, 2021. The OSC exercises its regulatory oversight function through the administration and enforcement of Ontario’s Securities Act and Commodity Futures Act, and administration of certain provisions of Ontario’s Business Corporations Act.
 
The OSC performs three distinct functions in support of its mandate:
  • Regulatory: making policies and rules.
  • Governance: serving as the board of directors.
  • Tribunal: administering and adjudicating proceedings before the Capital Markets Tribunal.
OSC Priorities
 
The OSC is responsible for setting its strategic direction and priorities and managing its operations. Each year, the organization is required to deliver a Statement of Priorities and Business Plan for the current fiscal year and an Annual Report.
 
Statutory Mandate
 
To provide protection to investors from unfair, improper, or fraudulent practices, to foster fair, efficient and competitive capital markets, and confidence in the capital markets, to foster capital formation, and to contribute to the stability of the financial system and the reduction of systemic risk.
 
About the Strategic Planning, Reporting and Execution Department
 
The Strategic Planning, Reporting and Execution Department is responsible for:
  • leading strategic and enterprise business planning;
  • facilitating and overseeing delivery of strategic initiatives;
  • and monitoring and reporting on corporate progress and performance to the Board, Ministry of Finance and the public.
Values
 
Professional | People | Ethical
 
Advancing Cooperation with Indigenous Peoples and Working to Understand and Integrate their Perspectives and Interests
 
As part of its phased approach to developing an action plan for truth and reconciliation, the OSC will continue to work collaboratively with Indigenous Peoples and organizations. The OSC is working to understand and integrate their perspectives and interests, as appropriate, in relevant areas of securities regulation and policy work, and improve engagement with Indigenous Peoples and organizations.
 
Inclusion & Diversity
 
The OSC is committed to diversity and provides an inclusive workplace where all employees feel safe, valued, respected, and empowered by ensuring a culture of inclusivity, diversity and equity. To support this commitment, the OSC has developed an active Pride Employee Group, Asian Employee Network (AEN), Black Employee Network (BEN), Parent & Caregiver, Jewish Employee Group, Neurodiverse Employee Network, and Inclusion & Diversity Council (IDC) that work together to represent diverse employee voices and perspectives and promote a supportive, inclusive experience for their colleagues.
 
The OSC is a proud partner with the following organizations:
  • Black North Initiative
  • Canadian Centre for Diversity and Inclusion
  • Pride at Work
  • Ascend Canada
Additional Information
 
Please visit the OSC website for more information about their mandate, as well as the current Board of Directors and Executive Team.
Experience:

Senior-level

Education Required:
Education/Certifications
  • Undergraduate or higher degree in project management, business administration, IT or related discipline or equivalent
  • PMP or equivalent
Salary Range:

Not Specified

Position description
The Opportunity
 
Reporting to the Vice President, Strategic Planning, Reporting and Execution (“VP”), the Head of the Strategic Project Management Office (“Head”) leads the build of a new enterprise Project Management Office (“PMO”) and team. This includes the development, implementation, and management of project management practices and enterprise portfolio projects, with a focus on aligning accountability and enabling strategic execution, managing portfolio governance, and overseeing high-impact projects.
 
This is a build and transformation mandate focused on establishing and scaling a fit-for-purpose PMO, while embedding portfolio discipline, transparency, and enterprise-wide alignment. The role operates as a strategic partner to the business, influencing and aligning stakeholders across project teams, executive leadership, the Board, and external partners. The Head will actively seek to drive productive change and buy-in, while leading the Strategic PMO responsible for enabling clear prioritization, strong execution rigor, and informed decision-making across the organization.
 
Key Responsibilities
 
Strategy, Planning & Framework Development
  • Design, build, and evolve the enterprise PMO, including recruitment and team build-out
  • Define the vision, priorities, and roadmap for the PMO, ensuring alignment with the OSC’s strategic plan, and incorporating input from key stakeholders
  • Develop and implement enterprise project management frameworks, standards, and methodologies in collaboration with IT, Finance, HR, Policy, and Risk teams
  • Lead change management and drive adoption of PMO tools, and best practices across the organization
  • Foster a culture of continuous improvement in project delivery
  • Strengthen planning discipline across the organization, improving the quality, consistency, and completeness of project plans
Project and Portfolio Management
  • Establish and oversee project delivery governance, ensuring clear objectives, accountabilities, budgets, KPIs, and risk management practices
  • Lead portfolio planning and prioritization to align resources with strategic priorities
  • Implement and manage project reporting for leadership and the Board, including regular updates and insights
  • Develop frameworks for resource management, financial oversight, risk/issue management, and decision-making
  • Oversee end-to-end portfolio delivery, identifying dependencies, constraints, and mitigation strategies
  • Design and implement consistent processes for project intake, business case development, and approvals
  • Ensure adherence to scope, budget, schedule, and quality standards across all initiatives
  • Provide oversight and guidance on project plans, documentation, and execution
  • Lead post-implementation reviews and embed lessons learned to support continuous improvement
  • Establish and maintain a centralized, reliable view of the project portfolio, including projects, resources, dependencies, and financials, to support transparency and decision-making
Cross-Functional Leadership & Stakeholder Engagement
  • Partner closely with executive leadership and stakeholders to build trust, embed the PMO function within the broader business, and ensure alignment on priorities, delivery, and decision-making
  • Collaborate with Finance, IT, and HR to implement integrated, fit-for-purpose project management practices
  • Facilitate effective communication between project teams and senior stakeholders to enable informed, timely decision-making
  • Engage with external stakeholders (e.g., CSA Secretariat, other jurisdictions) on portfolio delivery and governance
  • Lead, coach, and develop PMO staff, fostering a high-performing and collaborative team environment
Risk Management & Quality Assurance
  • Establish and implement a project risk framework aligned with enterprise risk management
  • Monitor, manage, and report on project risks, ensuring timely and effective mitigation
  • Define quality standards and oversee project audits and post-implementation reviews
  • Monitor PMO performance and drive continuous improvement in effectiveness and efficiency
Budgeting & Resource Allocation
  • Develop and oversee the PMO budget, ensuring effective allocation of resources
  • Partner with Finance to establish processes for tracking project financials and supporting business cases
  • Design and implement resource planning approaches to support portfolio delivery
Department Management, Team Leadership & Administration
  • Lead the PMO, including hiring, resource planning, and team development
  • Oversee day-to-day PMO operations, including budget, vendors, contracts, and reporting
  • Set and manage annual and long-term PMO priorities
  • Allocate and manage resources across projects, adjusting to evolving business needs
  • Lead performance management, coaching, and development of team members
Required skills / Experience
The Individual
The Head of the Strategic Project Management Office (“Head”) is a seasoned project delivery leader with a proven track record of building, operationalizing and leading fit-for-purpose Project Management Offices (PMOs) with complex, enterprise-wide project portfolios within regulated or similarly complex environments. The ideal candidate brings deep expertise in designing governance, frameworks, and processes that enable disciplined, transparent, and outcomes-driven execution.
 
They bring a combination of vision and delivery expertise, with strong capability across core project management disciplines, including portfolio governance, PPM tool implementation, resource planning, financial oversight, and risk management. The Head operates seamlessly across both strategic and hands-on execution, translating direction into clear, actionable outcomes, supported by strong communication and presentation skills for executive audiences.
 
A credible relationship builder and experienced people leader, this individual leads with integrity, taking a collaborative, consensus-driven approach to change — engaging stakeholders thoughtfully, building alignment, and fostering shared ownership rather than driving outcomes unilaterally. A pragmatic, proactive, and results-oriented operator, the Head brings sound judgment and strong problem, solving capabilities, with the ability to navigate complexity and drive a measured pace of change.
 
Key Qualifications
 
Technical Skills and Experience
  • 10+ years of proven experience leading and delivering project portfolios
  • Demonstrated ability to build, structure, and operationalize a Project Management Office (PMO) from the ground up, including day-to-day execution
  • Experience applying AI-enabled approaches to develop, optimize, and standardize project management frameworks and delivery processes
  • Proven experience in resource management, project financials, outcomes, and risk management
  • Experience providing direct performance feedback and mentorship to build high-functioning teams
  • Nuanced understanding of financial markets
  • Experience operating in a policy-driven, regulatory, or public sector environment is considered an asset
  • Experience scaling PMO or project delivery capabilities in evolving or complex environments
  • Expert knowledge in project management methodologies, principles, frameworks, and best practices
Personal Attributes
  • Proactive and practical mindset, with the ability to translate best practices into tailored frameworks and processes
  • Exceptional stakeholder management, communication, and interpersonal skills
  • Strong relationship builder with a collaborative and consensus-driven approach to change
  • High integrity, with a leadership style grounded in influence rather than authority
  • Proven problem-solving, sound judgement, and decision-making capabilities
  • Excellent people leadership and team management skills
  • Executive presence, with the ability to present effectively to boards, executives, and external stakeholders
  • Strong focus on execution, quality, and timelines, with the ability to prioritize and deliver in a dynamic, high-pressure environment
  • Strong analytical and critical thinking skills with a proactive and results-oriented mindset
Head of the Strategic Project Management Office
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How to Apply

Please apply online at the link below.

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