Associate Director, Special Loans

Winchesters; Toronto; On-site; CAD 150,000 - 165,000; Full time

Job summary

Winchesters in Toronto, ON, onsite (walking distance from Union) seeks an Associate Director of Insolvency/Restructuring to join the Commercial Lending team. Base salary $150,000 to $165,000 CAD with a large bonus, benefits, and other perks.

Reporting to the Vice President, Special Loans, you will manage a portfolio of underperforming loans, focusing on restructuring, execution, and risk mitigation. CPA with CIRP/LIT preferred.

Qualifications

• 3–5+ years in restructuring, insolvency, or related advisory.
• CPA designation with pursuit of CIRP and/or LIT designation preferred.
• Proficient in Microsoft Office.
• Strong communication, analytical thinking, and collaboration.

Responsibilities

• Resolve underperforming loan files with tailored workout and recovery strategies.
• Review mortgage loan structures in new deals.
• Contribute to Mortgage Credit Committee with risk-aware perspectives.
• Coordinate restructuring execution across workstreams with stakeholders.
• Collaborate with legal and professionals to advance files through restructuring processes.
• Monitor and resolve underperforming CMHC mortgages with the CMHC team.
• Own portfolio reporting and provide regular updates to senior stakeholders.

Education

CPA designation

CIRP or LIT designation (preferred)

Tools

Microsoft Office

Job description

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.