Managing Director, Strategic Operations & Portfolio Management

A unique leadership opportunity with a privately held Ontario-based group whose interests span businesses, investments, properties, philanthropy, and new ventures.

About the Opportunity

We are seeking an experienced and highly capable leader to work directly with the CEO in overseeing a diverse and evolving portfolio of businesses, investments, properties, philanthropic initiatives, and strategic projects.

This role serves as the central point of management across the portfolio, ensuring priorities remain aligned, initiatives move forward, stakeholders remain informed, and resources are effectively allocated.

Initially, the successful candidate will work closely alongside the CEO to develop a deep understanding of the organizations, relationships, and priorities. Over time, the role will progressively assume greater responsibility for operational oversight, project execution, financial management, and strategic initiatives.

This is an ideal opportunity for a senior leader who thrives in entrepreneurial environments and enjoys balancing strategy, execution, financial oversight, relationship management, and complex problem-solving.

KEY RESPONSIBILITIES:

• Act as a trusted strategic and operational partner to the CEO.
• Manage activities across multiple businesses, investments, projects, and initiatives.
• Ensure priorities, resources, and stakeholders remain aligned.
• Establish accountability, reporting structures, and operational processes.
• Identify risks, bottlenecks, and opportunities for improvement.

Financial, Business & Strategic Oversight

• Work closely with the CFO and external advisors to support financial planning, budgeting, cash flow management, investment oversight, insurance, tax planning, and capital allocation.
• Evaluate business opportunities, strategic initiatives, acquisitions, and investments.
• Support organizational growth, long-term planning, and portfolio performance.
• Oversee major projects and ensure successful execution across the portfolio.

Legal, Governance & Risk Management

• Coordinate legal matters and relationships with external advisors.
• Support governance, compliance, contractual obligations, and risk management activities.
• Ensure key business matters receive appropriate follow-up and execution.

Community & Philanthropic Initiatives

• Coordinate charitable, sponsorship, and community engagement activities.
• Support the execution of the CEO’s philanthropic priorities and partnerships.

Qualifications & Experience

• Bachelor’s degree in business, Finance, Commerce, Law, Economics, Public Administration, or a related field.MBA an asset
• 10+ years of progressive leadership experience.
• Experience within privately held companies, entrepreneurial organizations, family enterprises, investment groups, or multi-entity environments.
• Strong financial, operational, and strategic business acumen.
• Experience working with legal, financial, tax, insurance, and investment advisors.
• Exceptional organizational, leadership, communication, and problem‑solving skills.
• High degree of professionalism, discretion, and sound judgment.

Compensation will be commensurate with experience and reflective of the scope and complexity of the role.

A competitive executive compensation package, comprehensive benefits, professional development opportunities, and long-term growth potential will be offered to the successful candidate.

Why This Role Is Different

This position offers a rare opportunity to work directly with an entrepreneurial CEO while helping oversee a diverse portfolio of businesses, investments, properties, philanthropic initiatives, and future ventures.

For the right individual, this is more than a management role—it is an opportunity to become a trusted advisor, strategic partner, and key leader helping shape the future direction and success of a dynamic and evolving organization.