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Senior Investment Associate

Job in Toronto, Ontario, C6A, Canada
Listing for: Winchesters
Full Time position
Listed on 2026-02-13
Job specializations:
  • Finance & Banking
    Financial Analyst, Real Estate Finance, Corporate Finance, Financial Consultant
Salary/Wage Range or Industry Benchmark: 100000 - 125000 CAD Yearly CAD 100000.00 125000.00 YEAR
Job Description & How to Apply Below

The Senior Associate will play a critical role in evaluating, executing, and managing real estate investments across a diversified portfolio of income-producing properties. This position is heavily analytical and will support the full investment lifecycle, including underwriting, due diligence, financing analysis, and equity waterfall modeling.

The ideal candidate is a highly motivated real estate professional with strong financial modeling skills and experience working on complex transactions in a fast-paced investment environment.

Underwriting & Financial Analysis
  • Prepare and maintain detailed financial models for the acquisition, financing, and ongoing evaluation of real estate investments
  • Analyze operating cash flows, IRRs, equity multiples, and sensitivity scenarios
  • Assist in the preparation of internal investment materials and recommendations
  • Support ongoing portfolio valuation and performance monitoring
  • Coordinate and execute transaction due diligence for acquisitions and financings
  • Review financial statements, rent rolls, operating histories, capital expenditure plans, and third-party reports
  • Identify key investment risks and opportunities and summarize findings for senior leadership
  • Assist with transaction execution, including closing processes and documentation
Debt & Capital Markets Analysis
  • Analyze and model various debt structures, including acquisition, refinancing, and construction financing
  • Evaluate loan terms, covenants, DSCR, and refinancing scenarios
  • Support lender communications and financing submissions
Equity Waterfalls & Promote Modeling
  • Build and review complex equity waterfall and promote structures
  • Analyze investor returns under multiple capital stack and performance scenarios
  • Support investor reporting related to distributions and performance
Asset Management Support
  • Monitor asset performance relative to underwriting and business plans
  • Assist with budgeting, forecasting, and variance analysis
  • Support refinancing's, recapitalizations, and dispositions
Qualifications
  • 3–5 years of experience in real estate investments, private equity, acquisitions, or asset management
  • Advanced Excel and financial modeling skills
  • Experience with real estate underwriting, debt analysis, and equity waterfall/promote modeling
  • Strong understanding of income-producing real estate fundamentals
  • High attention to detail and strong organizational skills
  • Excellent written and verbal communication skills

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 the interview will be contacted.

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Position Requirements
10+ Years work experience
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