Analyst/Senior Analyst, Debt

Dream•Toronto, ON

13d•$75,000 - $110,000

About The Position

Dream is seeking an Analyst or Senior Analyst, Debt and Real Estate Finance to support the end‑to‑end management of our real estate debt portfolio, spanning origination, underwriting, execution, and ongoing portfolio management. This role is well‑suited for a real estate finance professional with a few years of hands‑on experience who is ready to operate independently, take ownership of a portfolio, and meaningfully contribute to financing strategy, decision‑making, and risk management.

Requirements

Bachelor’s degree in Finance, Real Estate, Accounting, or a related field
Approximately 2–5 years of relevant experience in real estate finance, commercial lending, debt advisory, mortgage servicing, REIT reporting, financial data analytics, or a related environment
Prior exposure to both transaction execution and post‑closing loan management is strongly preferred
Strong financial and analytical skills, with demonstrated experience in debt underwriting, cash flow analysis, and risk assessment
High level of proficiency in Excel (including financial modeling, sensitivity analysis, and data organization), with strong PowerPoint skills for clear, senior‑level communication
Solid understanding of loan documentation and ability to identify key commercial and risk considerations
Self‑directed and accountable, with ability to manage multiple workstreams independently without significant oversight
Strong communication and relationship‑building skills, both internally and with external lenders and advisors
Highly detail‑oriented, organized, and able to manage multiple priorities in a dynamic, transaction‑driven environment
Intellectual curiosity and a desire to grow into a broader debt origination and portfolio leadership role

Nice To Haves

Experience with development and/or multi‑asset portfolios is an asset

Responsibilities

Support and, over time, independently manage the origination and underwriting of debt for acquisitions, developments, redevelopments, and refinancings across the portfolio
Prepare detailed financial and risk analysis at the project, property, and portfolio level to support financing strategy and capital stack decisions
Develop high‑quality financing materials, including underwriting models, lender presentations, and confidential information memorandums (CIMs)
Evaluate and compare financing proposals, recommending optimal structures, terms, and lender counterparties
Coordinate and manage the debt closing process, including due diligence, documentation review, and satisfaction of lender funding conditions
Actively manage a portfolio of secured and corporate debt, maintaining a deep understanding of loan terms and structures
Manage construction loan draws, covenant compliance, refinancing timelines, interest rate exposure, maturity rollover risk, and repayments related to dispositions
Maintain and enhance debt databases and summaries to ensure accuracy of key terms, reporting requirements, and compliance tracking
Prepare portfolio‑level debt dashboards, analysis and insight for senior executives to support informed business decision‑making
Prepare quarterly and annual debt reporting deliverables to corporate accounting teams for their financial statement disclosures and MD&A of public REITs, as well as investor reporting for private equity vehicles. This includes debt continuity, scheduled repayments, debt valuation, interest rate sensitivity, and covenant compliance calculations
Coordinate lender reporting, consent requests, inquiries, and amendments
Partner closely with Accounting, Strategic Finance, Asset Management, and Development teams to support forecasting, refinancing scenarios, and business planning
Support internal reporting and executive materials with a forward‑looking, analytical lens
Contribute to process improvements, tools, and templates to enhance the long-term management of the debt portfolio
Assist with special projects and ad hoc analysis as the platform evolves