Job Description

At Old Oak:

We demonstrate integrity in everything we do We keep our people, our customers, and our community as our priority We are a company where people want to be

What We Offer:

Certified Great Place to Work Competitive wage structure Health and wellness benefits A company that gives back to the local community Opportunities for subsidized professional development Room for future growth and advancement A friendly, fun, and safe team-oriented work environment

Role Summary and Purpose

The Paralegal plays a critical role in supporting the property management team by providing licensed paralegal services in accordance with the Law Society of Ontario. This position focuses primarily on legal processes pertaining to the Residential Tenancies Act (RTA) and the Landlord and Tenant Board (LTB), including representation at hearings, preparation of legal documentation, and advising management on compliance and risk mitigation. The Paralegal also handles insurance administration and other risk management and compliance activities.

Responsibilities

Legal Proceedings Management:

Represent the company at the Landlord and Tenant Board and other tribunals, as permitted by the Law society of Ontario. Draft, prepare, and file legal documents including applications, notices, affidavits, and evidence packages. Maintain expertise in the Residential Tenancies Act and ensure compliance across all properties. Provide legal advice and guidance to property managers on landlord-tenant matters and regulatory compliance.

Tenant Relations & Communication:

Communicate with tenants regarding legal matters including arrears, compliance issues, and Board proceedings. Negotiate and document payment plans and settlements where appropriate. Serve as primary point of contact for tenants with respect to legal notices (e.g., N4, N5, N7, N9, N11, N12, N15).

Case & File Management:

Oversee legal records management in Yardi, SharePoint, and other platforms. Ensure all documentation is organized, up-to-date, and compliant with legal and regulatory requirements.

Compliance, Risk Management, & Insurance Administration:

Advise management on changes to legislation, tribunal processes, and case law affecting landlord-tenant matters. Develop internal procedures to mitigate legal risk and improve compliance efficiency. Track potential liability claims and liaison with insurance contacts and legal counsel as required. Conduct internal training sessions for managers and staff on legal processes and obligations.

Data Reporting & Oversight:

Track outcomes of LTB hearings and legal proceedings and report on trends, risks, and opportunities. Prepare and present regular reports regarding legal activity, arrears, and compliance matters.

Qualifications

Licensed Paralegal in good standing with the Law Society of Ontario (required). Minimum 2-3 years' experience practicing as a paralegal, preferably in residential property management or landlord-tenant law. Experience representing clients before the Landlord and Tenant Board preferred Strong knowledge of the RTA, LTB procedures, and relevant case law preferred. Skilled in legal drafting, advocacy, and negotiation. Proficient with property management software (Yardi preferred) and document management platforms (SharePoint, MS Suite). Strong organizational and communication skills, with attention to detail. Ability to manage a high-volume caseload while meeting deadlines.
Here at Old Oak, we are a quickly growing company and are excited to maintain the right staff. As such, we offer a very competitive compensation package to attract and maintain the best people. Old Oak is thankful to all who apply, however, only those who are qualified will be contacted for an interview.

Old Oak is an Equal Opportunity Workplace committed to fostering a safe, healthy, and inclusive work environment. We are committed to providing a fully accessible recruitment process. Accommodations are available upon request.

Job Types: Full-time, Permanent

Pay: From $65,000.00 per year

Benefits:

Company events Dental care Employee assistance program Extended health care Life insurance On-site parking Paid time off RRSP match Vision care
Experience:

paralegal: 2 years (required)
Licence/Certification:

Paralegal License (required)
Work Location: In person