Senior Director, Property Operations

Our client is seeking an experienced operational leader to oversee a diverse portfolio of high-value assets, facilities, infrastructure and operational activities across multiple environments within the Greater Toronto Area. This is a senior leadership opportunity for an individual who combines strong operational oversight, relationship management, vendor leadership, project execution and asset stewardship with a highly responsive, ownership-driven approach.

Reporting to executive leadership, the successful candidate will be responsible for ensuring the seamless operation, maintenance, performance, and continuous improvement of a broad and varied portfolio of assets. The role requires an individual who is equally comfortable providing strategic direction/oversight and personally engaging in day-to-day operational matters when required.

The role requires a highly organized, hands‑on operator who is comfortable managing multiple priorities simultaneously, leading vendors and contractors, overseeing capital initiatives, and operating in a fast‑paced, high‑accountability environment.

Your New Role

• Oversee the day‑to‑day operation, maintenance, and performance of a diverse portfolio of physical assets and operational environments.
• Lead and manage operational teams, and where necessary, act as the primary point of coordination across contractors, consultants, and service providers.
• Lead preventive maintenance programs, inspections, operational planning, and asset performance initiatives.
• Oversee capital projects, renovations, infrastructure upgrades, and operational improvement initiatives from planning through execution.
• Review scopes of work, contracts, budgets, and vendor proposals to ensure alignment with operational and financial objectives.
• Maintain direct involvement in operational matters, site activities, vendor coordination, inspections, troubleshooting, and issue resolution as required.
• Support executive leadership with operational reporting, planning, forecasting, and long‑term asset planning.
• Ensure exceptional responsiveness and execution across all aspects of the portfolio, balancing strategic priorities with immediate operational requirements.
• Foster a culture of accountability, service excellence, discretion, and continuous improvement.

What Sets You Apart

• 10+ years of operational leadership experience overseeing complex operations, residential operations, hospitality, facilities, private service operations, asset-intensive environments, or related asset-intensive sectors.
• A degree in Mechanical, Civil, or Electrical Engineering is preferred.
• Engineering, building systems, construction, facilities management, or related technical background preferred.
• Strong experience managing multiple concurrent assets, projects, vendors, consultants, contractors, and service providers.
• Operationally highly hands‑on with strong attention to detail and follow‑through.
• Highly responsive, solutions‑oriented, and comfortable operating within a fast‑paced environment.
• Strong communication skills, executive presence, and stakeholder management capabilities.
• Proven ability to prioritize effectively while managing multiple operational demands.
• Experience operating within high‑touch service environments, complex private operations, luxury assets or hospitality‑related settings is considered an asset.

What You Can Expect

This opportunity offers significant exposure, autonomy, long‑term growth potential within a dynamic and entrepreneurial environment. The client is open to considering candidates at both the Senior Director and Vice President level, depending on overall experience and leadership background.

Compensation will be competitive and aligned with the scope and seniority of the successful candidate.

Next Steps

If you are an operationally driven leader with experience overseeing high‑touch physical assets, vendors, capital projects, and service‑oriented environments — and you are looking to join a dynamic and entrepreneurial platform where responsiveness, ownership, and operational excellence are highly valued — we would welcome the opportunity to speak with you further.

If your background aligns with the qualifications and criteria outlined above, a member of the HighView Partners team will be in touch to discuss how we can help you make your Best Next Move.