Investment Associate

Toronto, ON
Hybrid
Posted Oct 31, 2026
1 position

$105,000–$125,000 / year

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Employment type: Full-time
Experience level: Mid-level · 2+ years
Minimum education: Bachelor’s degree
Posting language: English
Working hours: 40 hours per week
Office presence: 4 days per week
Seniority: Mid-Senior level
Application method: Apply on LinkedIn (LinkedIn sign-in required)

Job summary

Support real estate acquisitions and portfolio transactions through underwriting, due diligence, financial modeling, market research, and investment analysis. Monitor portfolio performance, prepare investor and lender reporting materials, assess new opportunities, and identify ways to improve analysis and reporting using AI and other technology.

Job details

Associate, Investments $105,000 – $125,000 Base + Bonus & Benefits Toronto, ON (4 days in office) Our client is a real estate organization with a diversified portfolio across multiple asset classes. They are seeking an Associate to join their Investments team, supporting acquisitions, financial modelling, investment analysis, investor reporting, and portfolio management. The role offers exposure to their growing seniors living platform, residential developments, and new investment opportunities. Responsibilities Investments & Acquisitions: Support the underwriting, due diligence, and execution of acquisitions and portfolio transactions, including financial modelling, operating projections, financing analysis, and investment returns. Financial Analysis & Modelling: Build and maintain financial models, conduct market research, and provide analytical support for existing investments, new projects, and corporate initiatives. Portfolio Monitoring: Monitor portfolio performance, evaluate market trends, and assist with investment strategy, risk assessment, and portfolio management. Investor Reporting: Coordinate information across various business units to prepare detailed reporting packages, investment materials, and updates for equity partners. Corporate & Project Financing: Prepare and coordinate financial information, due diligence materials, and reporting packages for lenders and financing partners. New Business Initiatives: Evaluate new business opportunities and investment strategies through financial modelling, market research, and preliminary investment analysis. Process Improvement & AI Integration: Identify opportunities to leverage AI and other technology to improve financial analysis, research, document review, and recurring reporting processes. Ad Hoc Projects: Provide financial and analytical support across various business units and special projects as required. Qualifications 3–5 years of relevant experience in real estate, investment banking, private equity, corporate finance, or management consulting. Undergraduate degree in Finance, Accounting, Business, or a related discipline. CFA, CPA, or other relevant professional designations considered an asset. Strong financial modelling and analytical capabilities, with advanced proficiency in Microsoft Excel. Experience with real estate investments, acquisitions, development, or portfolio management considered an asset. Strong understanding of financial statements, investment analysis, and corporate finance principles. Experience with AI tools and an interest in leveraging technology to improve research, analysis, and reporting processes. Coding or scripting experience is an asset. Excellent written and verbal communication skills, with the ability to synthesize complex financial information into clear and concise reporting materials. Strong attention to detail, organizational skills, and the ability to manage multiple priorities in a fast-paced environment. Proactive, self-motivated individual with strong problem-solving skills and the ability to work independently and collaboratively. To apply: Please send resumes directly to eric@winchesters.ca

What you’ll do

Requirements

Requires 3–5 years of relevant experience and an undergraduate degree in finance, accounting, business, or a related discipline; CFA, CPA, or another relevant designation is an asset. Candidates should have strong financial modeling and analytical skills, advanced Excel proficiency, knowledge of financial statements and corporate finance, and clear communication and organizational abilities; real estate experience, AI familiarity, and coding or scripting are assets.