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Investment Director
Investment DirectorWinchesters • Toronto, ON, Canada
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Investment Director

Investment Director

Winchesters • Toronto, ON, Canada
30+ days ago
Job type
  • Full-time
Job description

$150,000 base + very lucrative bonus

4 weeks’ vacation | 4 days per week in office – Downtown Toronto

Our client, a leading platform for commercial real estate lending and investment located in Downtown Toronto, is recruiting for an entrepreneurial and strategic Director, Real Estate Management.

This is an outstanding opportunity for an investment professional with deep portfolio management and underwriting expertise who wants to play a hands-on role in driving fund performance, managing capital, and designing new investment vehicles across both debt and equity.

You will work closely with the SVP and the Capital Markets team to shape fund strategy, oversee credit risk, and scale new lending initiatives. You will also have a set on the investment committee and be instrumental in the strategic vision of this group.

The Role

In this role, you will provide portfolio oversight and performance analysis across multiple investment vehicles, balancing disciplined credit underwriting with innovative fund strategies. You will manage treasury functions, optimize capital deployment, and support ongoing fund reporting and investor communications.

A key part of this role involves building and scaling the firm’s newest lending program, designed to rapidly deploy capital into shorter-term, high-quality commercial real estate loans. Additionally, you will collaborate with leadership to structure and launch new investment vehicles, including potential Debt Funds, Equity Funds, or REITs.

Key Responsibilities

  • Assist in treasury management across funds, optimizing capital deployment and liquidity.
  • Conduct portfolio analysis, performance tracking, and risk rating for the total portfolio.
  • Support ongoing fund reporting, investor communications, and compliance with investment policies.
  • Evaluate commercial real estate loan opportunities and provide recommendations to Investment Committees.
  • Review loan summaries, credit memos, and commitment letters.
  • Lead outreach to broker and borrower networks to identify lending opportunities.
  • Enhance policies, procedures, and reporting frameworks to strengthen credit governance.
  • Collaborate with the SVP to structure and launch new investment vehicles (e.g., Senior Debt, Self-Storage, Apartment REITs).
  • Work with legal counsel to structure and negotiate fund terms and investor agreements.
  • Support the setup of new entities, fund operations, and reporting infrastructure.

Requirements

  • Undergraduate degree in business or finance
  • 6+ years of experience in the commercial real estate industry (prior investment fund experience is an asset).
  • Advanced proficiency in Excel, PowerPoint, and Word with the ability to distill complex data into clear insights.
  • Strong ownership mindset with the confidence to engage investors and senior leadership.
  • Entrepreneurial spirit with the ability to manage multiple priorities in a high-growth environment.

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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Investment Director • Toronto, ON, Canada

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