Director of Property Operations

We’re looking for an experienced and highly organized Director of Property Operations to oversee the care, maintenance, and performance of multiple private residences and short-term rental properties. This leadership role is ideal for someone with a hands-on approach, deep operational knowledge, and strong vendor and project management skills.

Regular Responsibilities Include :

Property Oversight & Maintenance –You will manage the day-to-day operations of a diverse property portfolio, ensuring all systems, from HVAC to appliances, are proactively and responsively maintained. Responsibilities will include vendor scheduling, oversight, and performance management, fleet and seasonal readiness,and executing preventative maintenance programs. You’ll also identify and manage projects that improve the function, efficiency, or long-term value of each property.

Vendor Management & Procurement –Take the lead in sourcing and managing external service providers, ensuring quality work, timely delivery, and adherence to budgets. This includes developing accountability processes, negotiating pricing, managing contracts, and maintaining strong relationships across trades and services.

Leadership & Coordination – Provide direction, set standards, and coordinate work across household staff, vendors, and contractors to ensure smooth, professional operations. As the needs of the properties evolve, you’ll play a key role in scaling support and fostering a high-performance environment rooted in trust and clear expectations.

Short-Term Rental Operations – Oversee the maintenance and readiness of short-term rental units, including guest preparation, housekeeping schedules, inventory management, and seamless check-in / check-out experiences. Your work will ensure consistency, comfort, and quality across all stays.

Administrative & Family Support – Maintain detailed records of property operations, expenses, and project updates, reporting regularly to ownership. You may also support occasional errands, travel arrangements, or event-related logistics as needed.

What We’re Looking For :

• 5+ years of experience in residential property or estate management
• Strong leadership instincts and the ability to coordinate people and processes
• Experience managing vendors and overseeing maintenance and operational projects
• Proven skills in procurement, contract negotiation, and service quality oversight
• Highly organized with excellent attention to detail
• Comfort with digital tools, scheduling platforms, and reporting systems
• A valid driver’s license and availability for occasional evening or weekend needs

This is a rare and rewarding opportunity for a resourceful and experienced professional to take ownership of a high-quality, well-maintained property portfolio. You’ll work closely with ownership, contribute to long-term planning, and help build a culture of excellence and trust. If you take pride in well-run environments, value accountability, and enjoy building structure and efficiency behind the scenes, this could be the opportunity for you. Competitive compensation is offered based on experience.

This position requires a flexible schedule, with availability for occasional evenings and weekends. To apply, please send your cover letter and resume to Shardeigh McGillivray at shardeigh@venor.ca and Anna Bryant at anna@venor.ca.