Managing Director, Strategic Operations & Portfolio Management

London, ON
On-site
Posted Oct 10, 2026
1 position

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Employment type: Full-time
Experience level: Lead · 10+ years
Minimum education: Bachelor’s degree
Apply by: Apr 7, 2027
Posting language: English
Working hours: 40 hours per week
Seniority: Executive
Application method: Direct apply is available

Job summary

Partner with the CEO to oversee a diverse portfolio of businesses, investments, properties, philanthropic initiatives, and strategic projects, aligning priorities, resources, and stakeholders. Support financial and investment oversight, evaluate opportunities, manage major projects, and coordinate governance, legal, risk, and community initiatives.

Job details

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: Portfolio Leadership & Management 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 & Benefits 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.

What you’ll do

Requirements

Requires a bachelor’s degree in a relevant field and at least 10 years of progressive leadership experience; an MBA is an asset. Candidates should bring experience in privately held, entrepreneurial, family enterprise, investment group, or multi-entity environments, along with strong financial, operational, strategic, organizational, communication, and problem-solving capabilities.