Collections, Customer Experience, General Management, Operations, Property Management, Vendor Management

Compensation
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.

About The Role
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.

Key Responsibilities

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

Required Experience

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

Robust 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

Education Requirement





Bachelor’s degree required; Master’s degree preferred

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

Preferred Industry Background

Property management

Residential real estate operations

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

Technology Expectations
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.

What Success Looks Like
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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📌 Director of Operations (Ontario)
🏢 Royal York Property Management
📍 Ontario