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Investment Analyst, Real Estate
Toronto, ONDelivering a Better Hiring Experience.
At Outhire, we believe in revolutionizing the hiring process to make it more equitable and enjoyable for everyone involved. Our innovative approach puts candidates front and center, offering in-depth looks at open positions, personalized advice, and interview preparation. But we don't stop there - our Visual Resume feature ensures that hiring managers see the complete picture of who you are and what you bring to the table while eliminating biases you may face with traditional hiring practices. With Outhire, you can trust that we'll work tirelessly to match you with the role that truly fits your skills, experience, and aspirations. Join us in our mission to create a better hiring experience.
TITLE
Investment Analyst, Real Estate
SALARY RANGE
$80,000 – $100,000
CASH BONUS
Discretionary up to 20%
THE PERKS
Toronto, ON
THE OFFICE
Hybrid, 4-days a week
TEAM SIZE
6 people
THE ROLE
Working directly alongside the VP and President on a 6 person team to evaluate and execute real estate acquisitions across North America. This is a hands-on underwriting role where you are in the data rooms from day one — reviewing leases, building models, and presenting analysis that directly informs investment decisions. The team is flat, collaborative, and moves fast; the best meetings are spontaneous, and everyone has a seat at the table regardless of title.
Financial Modeling & Underwriting
A Toronto-based private investment firm backed by one of Canada's most prominent family offices, with a portfolio spanning real estate, private equity, and venture capital. The firm has deployed over $2.5 billion across signature projects including major retail redevelopments, professional sports franchise acquisitions, and national hospitality brand expansions. The investment team operates with institutional-calibre capital but an entrepreneurial culture.
THE OPPORTUNITY
The firm is seeing more deal flow right now than at any point in the past decade — actively deploying into income-producing real estate while many competitors sit on the sidelines. You'll underwrite everything from shopping centres in Western Canada to waterfront multifamily acquisitions in Toronto to US opportunities, all within the same quarter. Direct access to principals, real influence on investment decisions, and a variety of deal types that will accelerate your development faster than years at a larger institution. The firm values self-starters who bring ideas unprompted and thrive without heavy supervision.
EXPECTATIONS TIMELINE
By Month 1
ONLY QUALIFIED CANDIDATES WILL BE CONTACTED.
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At Outhire, we believe in revolutionizing the hiring process to make it more equitable and enjoyable for everyone involved. Our innovative approach puts candidates front and center, offering in-depth looks at open positions, personalized advice, and interview preparation. But we don't stop there - our Visual Resume feature ensures that hiring managers see the complete picture of who you are and what you bring to the table while eliminating biases you may face with traditional hiring practices. With Outhire, you can trust that we'll work tirelessly to match you with the role that truly fits your skills, experience, and aspirations. Join us in our mission to create a better hiring experience.
TITLE
Investment Analyst, Real Estate
SALARY RANGE
$80,000 – $100,000
CASH BONUS
Discretionary up to 20%
THE PERKS
- 3 weeks' vacation
- Extended Health Benefits
- Health and wellness spending account
- Continuing education support
Toronto, ON
THE OFFICE
Hybrid, 4-days a week
TEAM SIZE
6 people
THE ROLE
Working directly alongside the VP and President on a 6 person team to evaluate and execute real estate acquisitions across North America. This is a hands-on underwriting role where you are in the data rooms from day one — reviewing leases, building models, and presenting analysis that directly informs investment decisions. The team is flat, collaborative, and moves fast; the best meetings are spontaneous, and everyone has a seat at the table regardless of title.
- Financial Modeling & Underwriting (45%)
- Due Diligence & Acquisition Support (45%)
- Reporting (10%)
Financial Modeling & Underwriting
- Build and maintain sophisticated financial models in Excel for real estate acquisitions, developments, and financings
- Perform detailed cash flow analysis, valuation modeling, and return metrics including IRR, NPV, equity multiples, and sensitivity analyses
- Prepare and review ARGUS models for various property types to support underwriting and investment decisions
- Analyze lease structures, operating assumptions, and financing terms to ensure underwriting accuracy
- Model deal structures across varied transaction types including mezzanine loans, condo inventory opportunities, and commercial acquisitions
- Review data rooms and assess investment opportunities across multiple asset classes including retail, industrial, office, multifamily, land, and development
- Assist with the preparation of investment memoranda and presentations for senior management and stakeholders
- Work closely with internal teams and external partners including brokers, lenders, and consultants to evaluate opportunities and risks
- Analyze market data and comparable transactions to support investment recommendations
- Support deal evaluation across North American markets
- Present findings and investment recommendations to senior leadership
- Support internal reporting on deal activity and portfolio performance as needed
A Toronto-based private investment firm backed by one of Canada's most prominent family offices, with a portfolio spanning real estate, private equity, and venture capital. The firm has deployed over $2.5 billion across signature projects including major retail redevelopments, professional sports franchise acquisitions, and national hospitality brand expansions. The investment team operates with institutional-calibre capital but an entrepreneurial culture.
THE OPPORTUNITY
The firm is seeing more deal flow right now than at any point in the past decade — actively deploying into income-producing real estate while many competitors sit on the sidelines. You'll underwrite everything from shopping centres in Western Canada to waterfront multifamily acquisitions in Toronto to US opportunities, all within the same quarter. Direct access to principals, real influence on investment decisions, and a variety of deal types that will accelerate your development faster than years at a larger institution. The firm values self-starters who bring ideas unprompted and thrive without heavy supervision.
EXPECTATIONS TIMELINE
By Month 1
- Begin reviewing active deals and familiarize yourself with the firm's underwriting approach and internal processes
- Demonstrate the ability to independently navigate data rooms and extract key information for deal evaluation
- Build relationships with team members and develop an understanding of the firm's portfolio and investment strategy
- Independently underwrite deals with accuracy and sound analysis across multiple asset classes
- Manage several opportunities simultaneously, demonstrating strong organizational skills and attention to detail
- Provide thoughtful recommendations to senior leadership based on thorough financial analysis
- Show initiative in identifying potential issues and opportunities within deal materials
- Operate as a trusted, independent contributor requiring minimal oversight on standard deal evaluation
- Contribute to process improvements in financial modeling and underwriting workflows
- Handle varied and complex deal structures with confidence and sound judgment
- Serve as a reliable resource across all deal types and asset classes the firm pursues
- Demonstrate consistent accuracy and judgment that the team can depend on
- Take on increased complexity and contribute to strategic discussions around new opportunities
- Develop ARGUS proficiency if not already present at hire
- 2–5 years of real estate investment, underwriting, or financial analysis experience
- Strong Excel-based financial modeling skills, including cash flow projections for income-producing properties
- Experience with Argus is highly preferred
- Experience across multiple commercial real estate asset classes
- Excellent verbal and written communication skills
ONLY QUALIFIED CANDIDATES WILL BE CONTACTED.
WANT TO SEE MORE JOBS OR GET MORE DETAILS?
Not the right role for you? Interested but want to learn more before applying? Maybe you want to refer a friend?
Visit Outhire.ca and Sign Up to get earlier notices on upcoming jobs, full compensation details including range and benefits, full expectations timeline, real-time status updates and more.