08 Aug
Royal York Property Management
Oakville
Collections, Customer Experience, General Management, Operations, Property Management, Vendor Management
Type Full-Time
Location(s) Oakville, Ontario, Canada · Hybrid
Compensation CAD $135,000 - CAD $150,000 Annually
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Up to $200,000 CAD annually, including base salary and performance-based bonuses. Final compensation will be discussed during the interview process and will depend on experience, qualifications, leadership background, and overall fit.
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 property management company.
This is a senior leadership role with responsibility across people, process, service quality, financial discipline, technology, compliance, vendor management, and execution.
The Director of Operations will oversee managers and operational departments, improve performance, enforce service standards, strengthen reporting, and build scalable systems across the business.
Royal York manages single-family residential rental homes, which means operations involve owners, tenants, maintenance issues, rent payments, complaints, legal timelines, vendors, communication standards, and service expectations. The right candidate must be able to lead in a fast-moving environment where accountability, documentation, customer experience, and operational discipline all matter.
This role has the potential to grow into a COO-level position for the right person.
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
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
Solid 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
Preferred fields of study include Business Administration, Operations Management, Management, Finance,
Accounting, Economics, Real Estate, Engineering, Industrial Engineering, Supply Chain Management, Information Systems, Technology Management, or a related field
MBA, Master’s in Management, Master’s in Operations, or similar graduate degree is considered an asset
Property management experience is valuable, but it is not the only relevant background. Strong candidates may come from industries such as:
Property management
Leasing operations
Maintenance or field service operations
Telecom operations
Insurance claims or service operations
Automotive service operations
Financial services, collections, or receivables operations
Call centre or customer service operations
Logistics or dispatch operations
Hospitality or multi-location service businesses
Home services
Marketplace or platform-based operations
SaaS-enabled operations
Royal York is a tech-enabled property management company. The Director of Operations must be comfortable working with CRM systems, dashboards, automation, AI tools, customer portals, reporting platforms, and third-party technology partners.
This role does not require coding experience, but it does require the ability to work effectively with technical teams, explain operational problems clearly, and help improve systems that support the business.
Within the first 90 days, success should include stronger visibility into operational performance, improved reporting and scorecards, clearer service standards, stronger manager accountability, better escalation rules, and a practical plan to improve customer experience, profitability, compliance, and scalability.
Long term, the goal is for this person to help Royal York become more disciplined, more scalable, more profitable, more technology-enabled, and more consistent across every part of the operation.
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