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Winchesters
Associate Director, Special LoansWinchesters • Toronto, ON, Canada
Associate Director, Special Loans

Associate Director, Special Loans

Winchesters • Toronto, ON, Canada
11 days ago
Salary
CA$150,000.00 yearly
Job type
  • Full-time
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.
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Associate Director, Special Loans • Toronto, ON, Canada

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