Senior Investment Associate

Senior Associate / Associate – Special Loans / Insolvency Downtown Toronto – 4 days per week in office – Overtime expected

Our client manages capital on behalf of various partners, including banks, insurance companies, pension funds, family offices, credit unions, and individual investors.

We are seeking a Special Loans Associate or Sr. Associate who will be responsible for supporting the management, resolution, and reporting of underperforming, impaired, high-risk, or complex loans across the portfolio. The role sits within the Special Loans group and works directly with the VP, Special Loans to execute workout strategies, monitor borrower performance, coordinate stakeholder communication, and manage investor reporting obligations.

The role is execution-heavy and requires strong financial analysis, organizational discipline, communication skills, and attention to detail. The Analyst acts as the operational and analytical backbone of the Special Loans function, ensuring that strategies developed by the VP are implemented accurately and efficiently.

• Monitor a portfolio of watchlist, distressed, defaulted, and high-risk loans.
• Maintain detailed file‑level tracking for arrears, maturity status, covenant breaches, legal proceedings, borrower reporting obligations, recovery actions, property performance and enforcement milestones.
• Maintain accurate and current internal reporting trackers and dashboards.
• Ensure all file notes, borrower communications, investor updates, and action items are documented and organized.
• Coordinate and track conditions, deadlines, and deliverables across active files.
• Identify emerging risks and escalate material issues promptly.

• Execute strategies developed by the VP, Special Loans.
• Coordinate implementation of extensions, restructurings, forbearance arrangements, paydown strategies, enforcement actions, sales processes, refinancing strategies, and receivership and legal processes.
• Prepare file summaries, strategy memorandums, extension requests, and recovery analysis.
• Coordinate with legal counsel, receivers, brokers, consultants, appraisers, and other third‑party professionals.
• Monitor borrower compliance with negotiated agreements and reporting requirements.
• Track legal and enforcement costs, timelines, and recovery expectations.

• Serve as a day‑to‑day contact for investors on Special Loans files.
• Coordinate investor communications, updates, approvals, and information requests.
• Prepare investor reporting materials, including status updates, recovery summaries, cash flow reporting, strategy recommendations, extension requests and impairment commentary.
• Ensure investor communications are timely, accurate, and professionally presented.
• Coordinate investor consent processes and maintain records of approvals and responses.
• Support the VP, Special Loans in maintaining strong investor relationships during complex or stressed situations.

• Analyze borrower financial statements, rent rolls, appraisals, quantity surveyor reports, legal documentation, construction budgets, cash flow performance and recovery scenarios.
• Build and maintain financial models related to recovery analysis, payoff strategies, refinancing scenarios, liquidation outcomes, interest reserve analysis and sensitivity analysis.
• Assess collateral performance and debt recovery prospects.
• Assist in impairment and provisioning analysis where required.

• Work closely with Origination, Syndication, Funding & Servicing, Accounting and Executive Management.
• Coordinate internal approvals and ensure information flow across departments.
• Assist in preparation of management reporting and portfolio review materials.
• Support process improvement initiatives, reporting automation, and workflow standardization within the Special Loans group.

• Undergraduate degree in Finance, Commerce, Real Estate, Economics, Accounting or related field.
• 2–5+ years of experience.
• CPA, MBA, or CFA is preferred.
• Strong written communication and reporting skills.
• High attention to detail and organizational discipline.
• Ability to manage multiple complex files simultaneously.
• Strong follow‑through and responsiveness.
• Operates with urgency while maintaining accuracy.

If you are interested in learning more about this opportunity, please apply now. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.