Business Development, Customer Experience, Customer Success, Field Sales, Sales Type Full-Time Location(s) Oakville, Ontario, Canada · Field-Based Compensation CAD $70,000 - CAD $80,000 Annually Share this job: About Royal York Property Management

Royal York Property Management is a residential property management company serving property owners and tenants across Ontario. We manage residential rental properties throughout the tenancy lifecycle, with teams supporting leasing, tenant placement, maintenance coordination, rent administration, and day-to-day property operations. About the Role

Royal York Property Management is hiring a

Leasing Specialist

to drive leasing activity across

our portfolio of managed residential rental properties . This is a field-based, performance-driven role for someone who enjoys working with prospective renters and is motivated by closing deals and generating results. You will conduct property showings, engage with prospective renters, understand what they are looking for, address questions and objections, and actively work to convert interest into applications and offers. As part of Royal York's property management operation, you will also provide our internal teams with valuable feedback regarding renter interest, property presentation, market response, and other factors affecting vacancy. Key Responsibilities

Conduct scheduled showings at available properties within your assigned territory. Represent Royal York professionally when meeting prospective renters. Become familiar with available properties and communicate their features and rental terms effectively. Understand prospective renters' needs and position available properties accordingly. Build rapport and maintain strong communication throughout the leasing process. Address questions, hesitation, and objections that arise during showings. Identify reliable renter interest and confidently encourage prospects to move forward. Follow up with prospective renters and maintain momentum after property visits. Maintain accurate records of showings, prospect activity, and outcomes. Provide feedback on renter response, pricing concerns, and factors affecting leasing activity. Identify and report property condition, cleanliness, access, or readiness issues encountered in the field. Coordinate with Royal York's property management and leasing teams when required. Capture updated property photos or short videos as needed. Assist with rental marketing and other initiatives designed to increase interest in available properties. What We're Looking For

1–3 years of relevant experience

in residential leasing, real estate,



property management, rental housing, or sales. Previous experience working in a results-driven or commission-based environment is an asset. Solid sales instincts with the confidence to ask interested prospects to move forward. Ability to build rapport quickly and communicate effectively with prospective renters. Comfortable handling objections and navigating hesitation during the leasing process. Strong follow-up and organizational skills. Self-motivated and capable of managing a field-based schedule independently. Comfortable using smartphones, CRM systems, mobile applications, and digital leasing tools. Experience with rental advertising, property photography, video, or social media marketing is an asset. Reliable vehicle required. Flexible availability, including evenings and weekends based on leasing demand. About Royal York Property Management

Royal York Property Management is a residential property management company serving property owners and tenants across Ontario. We manage residential rental properties throughout the tenancy lifecycle, with teams supporting leasing, tenant placement, maintenance coordination, rent administration, and day-to-day property operations. About the Role

Royal York Property Management is hiring a

Leasing Specialist

to drive leasing activity across

our portfolio of managed residential rental properties . This is a field-based, performance-driven role for someone who enjoys working with prospective renters and is motivated by closing deals and generating results. You will conduct property showings, engage with prospective renters, understand what they are looking for, address questions and objections, and actively work to convert interest into applications and offers. As part of Royal York's property management operation, you will also provide our internal teams with valuable feedback regarding renter interest, property presentation, market response, and other factors affecting vacancy. Key Responsibilities

Conduct scheduled showings at available properties within your assigned territory.

Represent Royal York professionally when meeting prospective renters.

Become familiar with available properties and communicate their features and rental terms effectively.





Understand prospective renters' needs and position available properties accordingly.

Build rapport and maintain strong communication throughout the leasing process.

Address questions, hesitation, and objections that arise during showings.

Identify serious renter interest and confidently encourage prospects to move forward.

Follow up with prospective renters and maintain momentum after property visits.

Maintain accurate records of showings, prospect activity, and outcomes.

Provide feedback on renter response, pricing concerns, and factors affecting leasing activity.

Identify and report property condition, cleanliness, access, or readiness issues encountered in the field.

Coordinate with Royal York's property management and leasing teams when required.

Capture updated property photos or short videos as needed.

Assist with rental marketing and other initiatives designed to increase interest in available properties.

What We're Looking For

1–3 years of relevant experience

in residential leasing, real estate, property management, rental housing, or sales.

Previous experience working in a results-driven or commission-based workplace is an asset.

Strong sales instincts with the confidence to ask interested prospects to move forward.

Ability to build rapport quickly and communicate effectively with prospective renters.

Comfortable handling objections and navigating hesitation during the leasing process.

Strong follow-up and organizational skills.

Self-motivated and capable of managing a field-based schedule independently.

Comfortable using smartphones, CRM systems, mobile applications, and digital leasing tools.

Experience with rental advertising, property photography, video, or social media marketing is an asset.

Reliable vehicle required.

Flexible availability, including evenings and weekends based on leasing demand.

Compensation

100% Commission – Uncapped Earning Potential This is a

100% commission-based position

designed for motivated Leasing Specialists who want their earnings directly connected to their individual performance. There is

no cap on earning potential . The more successful leases you generate, the greater your opportunity to earn. This compensation model is best suited to someone who is confident in their sales and closing abilities, comfortable working in a performance-driven environment, and motivated by the opportunity to increase their income through results. Over 40 Locations In Canada And 11 Locations In Europe #J-18808-Ljbffr

📌 Leasing Specialist (Winnipeg)
🏢 Royal York Property Management
📍 Winnipeg