Director of Operations

Royal York Property Management is hiring a highly experienced Director of Operations to lead and strengthen the day-to-day operations of a growing, service-driven residential property management company.

This is a senior leadership role for someone who can manage people, process, service quality, financial discipline, technology, compliance, vendor management, reporting, and execution across multiple departments.

The Director of Operations will oversee managers and operational teams, improve performance, enforce service standards, strengthen reporting, and build scalable systems across the business.

This role is for someone who can lead in a fast-moving environment where owners, tenants, maintenance issues, rent payments, complaints, legal timelines, vendors, documentation, customer experience, and operational discipline all matter.

How to Apply

• Apply with your resume
• If your background aligns, you’ll receive a link to a short pre-recorded video interview shortly after applying
• Candidates selected after the pre-recorded interview may be contacted regarding next steps

What You’ll Do

• Lead managers, team leads, and operational departments
• Improve operating processes, service standards, and team accountability
• Ensure owners, tenants, vendors, and internal teams receive clear and timely communication
• Enforce service standards across maintenance, leasing, collections, complaints, escalations, and customer communication
• Strengthen rent collection, payment follow-up, receivables discipline, and financial accountability
• Improve documentation, compliance, legal escalation, and risk-control processes
• Build dashboards, scorecards, reporting systems, and management routines
• Audit CRM and operational data to ensure reports reflect business reality
• Identify root causes when performance drops and implement corrective action
• Work with CRM systems, automation, AI tools, customer portals, dashboards, and third-party platforms
• Translate operational problems into clear requirements for technical teams and software partners
• Manage vendors, service providers, software vendors, and cross-company partnerships
• Control costs while protecting service quality, compliance, collections, and customer experience
• Coach, develop, restructure, or replace managers when required
• Support long-term operational scalability, consistency, profitability, and technology adoption

Requirements

• 10+ years of operations leadership experience
• 5+ years in a senior operations role managing managers, department heads, or multiple operational teams
• Experience leading a high-volume, people-heavy service operation
• Experience overseeing teams of 50+ people, either directly or through managers, team leads, contractors, vendors, or distributed operational staff
• Strong experience with customer experience, service delivery, process improvement, team accountability, and operational performance
• Experience with collections, payment follow-up, receivables, financial accountability, or payment-related operating controls
• Strong judgment around documentation, compliance, escalation, risk control, and operational discipline
• Experience with CRM systems, dashboards, workflow tools, reporting, automation, or AI-enabled systems
• Experience managing vendors, partners, external service providers, software vendors, or cross-company relationships
• Ability to work with technical teams and translate business needs into clear system, workflow, automation, or reporting requirements
• Bachelor’s degree required
• Strong leadership, communication, organization, problem-solving, and accountability skills

Nice-to-Have

• Master’s degree, MBA, or graduate degree in management, operations, business, finance, technology, or a related field
• Education in Business Administration, Operations Management, Finance, Accounting, Economics, Real Estate, Engineering, Industrial Engineering, Supply Chain Management, Information Systems, or Technology Management
• Property management, residential real estate operations, leasing operations, or maintenance operations experience
• Experience in telecom, insurance claims, automotive service, financial services, collections, call centre operations, logistics, dispatch, hospitality, home services, marketplaces, SaaS-enabled operations, or platform-based businesses
• Experience improving reporting, scorecards, dashboards, escalation rules, manager accountability, and operating cadence
• Experience working in a founder-led, high-growth, service-based company

Ideal Candidate

The ideal candidate is a senior operator who can manage people, systems, service quality, financial discipline, and execution at the same time.

They are comfortable leading managers, improving processes, using data, holding teams accountable, and making difficult decisions when performance is not where it needs to be.

They understand that strong operations require clear standards, clean reporting, strong follow-up, accurate documentation, and consistent execution.

They can work with technical teams without needing to code. They know how to explain operational problems clearly and help build better workflows, automations, dashboards, and systems.

They are calm under pressure, direct, organized, and able to bring structure to a fast-moving environment with many competing priorities.

Important Location Requirement

This is a hybrid position, with GTA-based candidates preferred. The successful candidate must be available to attend a local office, meeting, training session, or company event if requested.

Please only apply if you are based in Ontario or are willing and able to commute or relocate to the GTA.

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