Managing Director - Portfolio Operations

Location: Winnipeg, Manitoba
Compensation: $150,000–$200,000 per year
Travel: Approximately 1 day every 2 weeks

About the Role

Staffmax is seeking an experienced Managing Director to oversee the operations and performance of a portfolio of privately held companies across Canada.

This is a hands-on operating role for an experienced business leader who knows how to run medium-sized industrial businesses and is comfortable working directly with both senior leadership and frontline, blue-collar teams.

The successful candidate will initially oversee a smaller number of businesses, with responsibility expected to grow to approximately 4–6 companies within the first year . The portfolio includes businesses in manufacturing, construction, and distribution , with operations in Winnipeg, the Greater Toronto Area, Saskatchewan, and other locations across Canada.

This is not a traditional finance-focused private equity position. We are looking for an operator who can take ownership of business performance, make difficult decisions, manage people at all levels of an organization, and drive results.

Key Responsibilities

Portfolio & P&L Ownership

• Take overall responsibility for the financial and operational performance of portfolio companies.
• Maintain a strong understanding of P&L, balance sheets, cash flow, and key business metrics .
• Identify opportunities to improve profitability, efficiency, productivity, and overall business performance.
• Work directly with General Managers and Controllers to establish priorities and drive accountability.
• Report to the Senior Managing Director on company performance, risks, opportunities, and strategic initiatives.

Leadership & People Management

• Provide high-level leadership and direction to General Managers and Controllers.
• Recruit, hire, and develop key leadership positions, including GMs and Controllers.
• Establish compensation structures and bonus plans for key personnel.
• Make difficult personnel decisions when required, including major or mass terminations.
• Lead organizations through periods of change, restructuring, and operational improvement.
• Be comfortable managing and communicating directly with blue-collar employees, tradespeople, and shop-floor teams .

Operations & Capital Investment

• Oversee day-to-day operational performance through General Managers and leadership teams.
• Evaluate and approve major CAPEX, equipment purchases, facility investments, and other significant expenditures .
• Work with leadership teams to improve production, efficiency, staffing, and operational processes.
• Step into businesses when necessary to stabilize operations or address significant performance issues.

External Relationships

• Develop and maintain relationships with banks, major vendors, customers, and other key stakeholders.
• Represent portfolio companies in significant commercial and operational matters.
• Support acquisitions, integrations, expansions, and other strategic initiatives as required.

What We're Looking For

The ideal candidate is an experienced operator who has successfully run a medium-sized industrial, manufacturing, construction, or distribution business.

You should be someone who:

• Has significant experience running operations , not simply advising them.
• Has owned or been heavily responsible for a company's P&L and financial performance .
• Has directly managed blue-collar employees, tradespeople, or shop-floor personnel .
• Has experience hiring and terminating frontline employees.
• Is comfortable making difficult decisions, including workforce reductions when necessary.
• Has strong financial literacy and can confidently understand and challenge a P&L and balance sheet.
• Has experience managing General Managers, Controllers, or other senior leaders.
• Can operate independently and take full ownership of business outcomes.
• Is comfortable working across multiple companies and locations.
• Has strong communication, leadership, negotiation, and problem-solving skills.
• Is willing and able to travel approximately one day every two weeks .

Preferred Qualifications

• P.Eng. designation
• MBA
• Experience in manufacturing, construction, distribution, or other industrial environments.
• Experience overseeing multiple business units or companies.
• Experience working within a private equity, family-owned, or privately held business environment.

The Opportunity

This is an opportunity for a proven operator to take on significant responsibility across a growing portfolio of Canadian businesses.

The successful candidate will have the autonomy and authority to identify problems, make decisions, implement change, and drive results across multiple operating companies.

If you are an experienced General Manager, COO, President, VP Operations, or similar senior operating leader who enjoys getting into the business and making things happen, we would like to hear from you.

Compensation: $150,000–$200,000 annually