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Winchesters

Associate Director, Special Loans

Toronto, ON, Canada

$150,000 to $165,000 CAD / year · Full-time

Within 25 km of Vaughan · About 22.9 km from the city centre

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Job details

Pay: $150,000 to $165,000 CAD / year
Job type: Full-time
Apply by: Nov 12, 2026
Experience: 3–5+ years of relevant professional experience, ideally within restructuring, insolvency, or a related advisory environment.
Posted: Oct 13, 2026

Original job description

Associate Director, Insolvency/Restructuring (Commercial Mortgage Lending)

Toronto, ON - onsite (walking distance from Union)

$150,000 to $165,000 base salary plus large bonus, benefits, and other perks

Our client is a Canadian private equity firm which creates and co-invests in real estate investment solutions to deliver sustainable, premium risk-weighted returns. They have grown in a number of their funds and continue to seek further opportunities to invest across the whole portfolio.

Our client is seeking an Associate Director of Insolvency/Restructuring to join their Commercial Lending team. Reporting to the Vice President, Special Loans, this role will work closely with senior stakeholders to manage and resolve a portfolio of underperforming loans, with a focus on restructuring, execution, and risk mitigation.

Responsibilities

Resolve underperforming loan files by evaluating, recommending, and executing tailored workout and recovery strategies.
Review and assess mortgage loan structures in new deals.
Actively contribute to the Mortgage Credit Committee by providing informed, risk-aware perspectives on new transactions and highlighting emerging concerns.
Partner closely with internal stakeholders to coordinate execution of restructuring strategies, ensuring alignment, accountability, and timely decision-making across all workstreams.
Coordinate with legal and other professional partners to advance files through formal legal restructuring processes.
Partner with the CMHC team to monitor and resolve underperforming CMHC mortgages.
Own ongoing portfolio reporting and provide regular performance updates to senior stakeholders.

Requirements

3–5+ years of relevant professional experience, ideally within restructuring, insolvency, or a related advisory environment.
CPA designation with active pursuit of CIRP and/or Licensed Insolvency Trustee (LIT) designation preferred.
Proficient in Microsoft Office (Outlook, Word, Excel, PowerPoint).
Adaptable and decisive, able to pivot quickly and perform under pressure.
Strategic, analytical thinker with a collaborative mindset and ownership mentality.
Excellent communication and presentation skills across all levels.

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.

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More about this job

Responsibilities

Manage and resolve underperforming commercial mortgage loans by assessing and executing tailored restructuring, workout, and recovery strategies, while mitigating risk and coordinating formal legal processes. Contribute to credit committee decisions, collaborate with internal teams and external partners, monitor CMHC mortgages, and report portfolio performance to senior stakeholders.

Requirements

Requires 3–5+ years of relevant experience, ideally in restructuring, insolvency, or a related advisory environment; a CPA designation is noted, with CIRP and/or Licensed Insolvency Trustee credentials preferred. Candidates should be proficient in Microsoft Office and demonstrate adaptability, decisiveness, analytical and strategic thinking, collaboration, ownership, and strong communication and presentation skills.

Skills

Loan Restructuring
Insolvency
Commercial Mortgage Lending
Loan Workout Strategies
Recovery Strategies
Risk Mitigation
Mortgage Credit Analysis
Portfolio Management
Financial Analysis
Legal Restructuring
Portfolio Reporting
Stakeholder Management
Communication
Presentation Skills
Microsoft Office
CPA

Benefits

Benefits
Large Bonus
Other Perks

Visa sponsorship

Not detected in the job text

Keywords

Commercial Mortgage Lending
Insolvency
Restructuring
Special Loans
Underperforming Loans
Loan Workout
Recovery Strategies
Risk Mitigation
Mortgage Loan Structures
Mortgage Credit Committee
CMHC Mortgages
Legal Restructuring
Portfolio Reporting
CPA
CIRP
Licensed Insolvency Trustee
Microsoft Office
Outlook
Word
Excel
PowerPoint
Stakeholder Management
Financial Services
Real Estate
Private Equity

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