About Us
O’Shanter is a well-established Toronto-based real estate development and property management company with a long-standing reputation for quality, integrity, and community service and leadership. We are proudly ISO certified for Quality and Environmental Management and recognized as a Great Place to Work®, as well as one of Canada’s Best Workplaces in Real Estate & Construction.
Job Summary
O’Shanter Development Company Ltd. is seeking a Tenant Arrears & Recovery Specialist who is responsible for the recovery of outstanding rent, damage claims, and other tenant-related receivables arising from former tenancies. Reporting to and working closely with In-House Counsel, this role combines collections expertise, tenant arrears management, skip tracing, and legal file coordination to maximize recoveries while ensuring compliance with applicable legislation and company policies.
The successful candidate will be a highly organized, results-oriented professional with experience in skip tracing, collections, landlord-tenant matters, or legal recovery environments. This position requires strong communication, negotiation, investigative, and documentation skills.
Key Responsibilities
Collections & Recovery
- Manage an assigned portfolio of former tenant arrears and recovery files.
- Conduct professional collection activities through telephone, email, written correspondence, and other approved communication channels.
- Negotiate repayment arrangements and settlement agreements within established authority limits.
- Monitor payment arrangements and follow up on overdue commitments.
- Identify opportunities to maximize recoveries while maintaining professionalism and compliance.
Skip Tracing & Investigations
- Conduct skip tracing and investigative efforts to locate former tenants using available databases, public records, and other lawful sources.
- Verify contact information and assess collectability of accounts.
- Prioritize recovery efforts based on account age, balance outstanding, and likelihood of recovery.
Legal Coordination
- Work closely with and under the direction of the In-House Counsel on accounts requiring legal review or escalation.
- Assist in the preparation and organization of documentation for Landlord and Tenant Board (LTB) proceedings, Small Claims Court matters, enforcement actions, and collection litigation.
- Maintain complete and accurate file documentation to support legal proceedings and recovery efforts.
- Recommend accounts for legal escalation, settlement, write-off, or other recovery strategies.
Documentation & Reporting
- Maintain detailed, accurate, and audit-ready records of all collection activities, communications, payment arrangements, and recovery actions within Yardi or other designated systems.
- Prepare regular performance and portfolio reports (weekly), including: Former tenants successfully located, Amounts recovered, Amounts contacted, Payment arrangements established, Payment arrangement compliance, Recommended legal escalations, Portfolio recovery trends
Compliance
- Ensure all collection and recovery activities are conducted in accordance with applicable legislation, including the Residential Tenancies Act (Ontario), privacy requirements, company policies, and legal directives.
- Maintain confidentiality of tenant, legal, and corporate information at all times.
Performance Expectations
Success in this role will be measured through (KPIs):
- Recovery rate on assigned portfolio
- Skip tracing effectiveness and tenant location success rate
- Number of meaningful debtor contacts achieved
- Conversion of contacts into payment arrangements or recoveries
- Reduction of aged receivables balances
- Quality and accuracy of documentation
- Timeliness of account follow-up and legal escalation recommendations
Qualifications & Experience
- Minimum 3–5 years of experience in collections, tenant arrears recovery, legal collections, credit recovery, or a related field.
- Criminal background check and credit assessment. *
- Experience within residential property management, landlord-tenant services, legal recovery, or enforcement environments is strongly preferred.
- Working knowledge of Ontario landlord-tenant processes and Landlord and Tenant Board procedures.
- Experience supporting legal counsel, paralegals, or litigation recovery activities is considered a strong asset.
- Strong negotiation, communication, and conflict-resolution skills with English language proficiency
- Exceptional attention to detail and documentation standards.
- Ability to work independently while collaborating effectively with legal and operational teams.
- Proficiency with Yardi or similar property management/accounting systems is preferred.
What we offer:
- We offer a competitive compensation structure designed to reward performance and recovery results.
- Base compensation: $21.00 – $29.00 per hour, depending on experience and qualifications plus commission.
- Performance-based recovery incentive program.
- Flexible engagement structure (part-time contract or full-time employment for the right candidate; also hybrid or onsite work as required).
- Opportunity to work closely with legal counsel on sophisticated recovery and enforcement matters.
The final compensation package will be determined based on relevant experience in skip tracing effectiveness, tenant arrears recovery, collections, landlord-tenant matters, legal coordination, and overall qualifications.
Must be legally authorize to work in Canada.
Pay: $21.00-$29.00 per hour
Benefits:
- Company events
- Dental care
- Disability insurance
- Extended health care
- Flexible schedule
- Life insurance
- Paid time off
- Tuition reimbursement
- Vision care
- Work from home
Work Location: Hybrid remote in Toronto, ON M4M 2S1
