Delivering 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.TITLEInvestment Analyst, Real EstateSALARY RANGE$80,000 – $100,000CASH BONUSDiscretionary up to 20%THE PERKS3 weeks' vacationExtended Health BenefitsHealth and wellness spending accountContinuing education supportLOCATIONToronto, ONTHE OFFICEHybrid, 4-days a weekTEAM SIZE6 peopleTHE ROLEWorking 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 meetingsare spontaneous, and everyone has a seat at the table regardless of title.Financial Modeling & Underwriting (45%)Due Diligence & Acquisition Support (45%)Reporting (10%)THE TASKSFinancial Modeling & UnderwritingBuild and maintain sophisticated financial models in Excel for real estate acquisitions, developments, and financingsPerform detailed cash flow analysis, valuation modeling, and return metrics including IRR, NPV, equity multiples, and sensitivity analysesPrepare and review ARGUS models for various property types to support underwriting and investment decisionsAnalyze lease structures, operating assumptions, and financing terms to ensure underwriting accuracyModel deal structures across varied transaction types including mezzanine loans, condo inventory opportunities,



and commercial acquisitionsDue Diligence & Acquisition SupportReview data rooms and assess investment opportunities across multiple asset classes including retail, industrial, office, multifamily, land, and developmentAssist with the preparation of investment memoranda and presentations for senior management and stakeholdersWork closely with internal teams and external partners including brokers, lenders, and consultants to evaluate opportunities and risksAnalyze market data and comparable transactions to support investment recommendationsSupport deal evaluation across North American marketsReportingPresent findings and investment recommendations to senior leadershipSupport internal reporting on deal activity and portfolio performance as neededTHE COMPANYA 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 OPPORTUNITYThe 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 TIMELINEBy Month 1Begin reviewing active deals and familiarize yourself with the firm's underwriting approach and internal processesDemonstrate the ability to independently navigate data rooms and extract key information for deal evaluationBuild relationships with team members and develop an understanding of the firm's portfolio and investment strategyBy Month 3Independently underwrite deals with accuracy and sound analysis across multiple asset classesManage several opportunities simultaneously, demonstrating strong organizational skills and attention to detailProvide thoughtful recommendations to senior leadership based on thorough financial analysisShow initiative in identifying potential issues and opportunities within deal materialsBy Month 6Operate as a trusted, independent contributor requiring minimal oversight on standard deal evaluationContribute to process improvements in financial modeling and underwriting workflowsHandle varied and complex deal structures with confidence and sound judgmentBy Month 12Serve as a reliable resource across all deal types and asset classes the firm pursuesDemonstrate consistent accuracy and judgment that the team can depend onTake on increased complexity and contribute to strategic discussions around recent opportunitiesDevelop ARGUS proficiency if not already present at hireTHE SKILL SET2–5 years of real estate investment, underwriting, or financial analysis experienceStrong Excel-based financial modeling skills, including cash flow projections for income-producing propertiesExperience with Argus is highly preferredExperience across multiple commercial real estate asset classesExcellent verbal and written communication skillsONLY 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.

📌 Investment Analyst, Real Estate - $80,000 - $100,000 A Year (Toronto)
🏢 Outhire
📍 Toronto