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 qualified experience, ideally within restructuring, insolvency, or a related advisory environment.
- CPA designation
- 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.

📌 Associate Director Restructuring and Insolvency (Toronto)
🏢 Winchesters
📍 Toronto