Real Estate Underwriting Analyst
Obra Real Estate, Chicago, IL, United States
Obra Real Estate (“ORE”) is a commercial real estate lending platform focused on bridge and special‑situations financing for middle‑market transitional assets. ORE originates and holds loans on balance sheet, targeting transactions typically ranging from $5 million to $75 million across multifamily, industrial, retail, and office properties.
ORE is a subsidiary of Obra Capital, a differentiated alternative asset management firm with expertise across structured credit, insurance‑linked strategies, and asset‑based investments. ORE’s mission is to build a premier, institutional‑quality commercial real estate lending platform.
Position Overview ORE is seeking a Real Estate Underwriting Analyst to support our originations and investment teams. In this role, you will play a critical part in evaluating new investment opportunities, driving transactions from initial underwriting through closing, and supporting the firm’s continued growth. This person will be responsible for financial underwriting, due diligence, risk assessment, and preparation of investment materials for review by senior management and the investment committee. Success in this role requires strong analytical judgment, attention to detail, and the ability to evaluate and mitigate risk in complex, time‑sensitive transactions.
Responsibilities
Underwrite and produce valuations for commercial real estate assets, with a primary focus on multifamily, industrial, retail, and office properties
Build and maintain detailed financial models, including cash flow analysis, sensitivity analyses, and return metrics
Evaluate loan structures, collateral quality, sponsor strength, and downside risk
Conduct and coordinate due diligence to validate underwriting assumptions, including review of third‑party reports, leases, operating statements, and borrower materials
Perform market research and analysis to assess local supply/demand dynamics, rents, vacancies, and comparable transactions
Engage with brokers, sponsors, and other local market participants to verify transaction assumptions
Prepare clear, comprehensive investment memoranda outlining the transaction structure, risks, mitigants, and investment thesis
Present transaction analyses to internal stakeholders and support the investment committee approval process
Collaborate with executive management on investment decisions
Work closely with legal counsel on deal structuring and review of loan documentation
Support the deal team through closing, including coordination with internal and external stakeholders
Assist with ad hoc analyses, research, and special projects as needed
Collaborate with other teams within Obra Real Estate and the broader Obra Capital platform
Qualifications & Requirements
Minimum of 2 years of relevant experience in commercial real estate, real estate lending, investment banking, private credit, or finance
Bachelor’s degree from a top‑50 university (real estate, finance, economics, or related field preferred)
Candidates local to Chicago strongly preferred
Strong financial modeling and analytical skills with the ability to draw independent conclusions
Proficiency in Microsoft Excel, PowerPoint, and Word
Strong written and verbal communication skills
High level of attention to detail, organization, and accountability
Entrepreneurial mindset with a strong desire to help build and grow a platform
In‑office role, 5 days per week, at ORE’s downtown Chicago office
Occasional travel for site visits and industry conferences
The expected base salary range for this role is outlined below. In addition to the base salary, total compensation may include a discretionary bonus based on performance. This range reflects a variety of factors, including years of relevant experience, education, and other qualifications pertinent to the position.
$70,000 - $100,000
The firm also offers robust Benefits offerings which include Comprehensive Medical/Rx, Dental and Vision plans; 401(k) program with company match; Flexible Savings Accounts (FSA); Healthcare Savings Accounts (HSA) with company contribution; Basic and Voluntary Life Insurance; Long-Term Disability (LTD) and Short-Term Disability (STD) insurance; and Commuter Benefits plan. In addition all employees of Obra are provided with a daily lunch stipend.
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ORE is a subsidiary of Obra Capital, a differentiated alternative asset management firm with expertise across structured credit, insurance‑linked strategies, and asset‑based investments. ORE’s mission is to build a premier, institutional‑quality commercial real estate lending platform.
Position Overview ORE is seeking a Real Estate Underwriting Analyst to support our originations and investment teams. In this role, you will play a critical part in evaluating new investment opportunities, driving transactions from initial underwriting through closing, and supporting the firm’s continued growth. This person will be responsible for financial underwriting, due diligence, risk assessment, and preparation of investment materials for review by senior management and the investment committee. Success in this role requires strong analytical judgment, attention to detail, and the ability to evaluate and mitigate risk in complex, time‑sensitive transactions.
Responsibilities
Underwrite and produce valuations for commercial real estate assets, with a primary focus on multifamily, industrial, retail, and office properties
Build and maintain detailed financial models, including cash flow analysis, sensitivity analyses, and return metrics
Evaluate loan structures, collateral quality, sponsor strength, and downside risk
Conduct and coordinate due diligence to validate underwriting assumptions, including review of third‑party reports, leases, operating statements, and borrower materials
Perform market research and analysis to assess local supply/demand dynamics, rents, vacancies, and comparable transactions
Engage with brokers, sponsors, and other local market participants to verify transaction assumptions
Prepare clear, comprehensive investment memoranda outlining the transaction structure, risks, mitigants, and investment thesis
Present transaction analyses to internal stakeholders and support the investment committee approval process
Collaborate with executive management on investment decisions
Work closely with legal counsel on deal structuring and review of loan documentation
Support the deal team through closing, including coordination with internal and external stakeholders
Assist with ad hoc analyses, research, and special projects as needed
Collaborate with other teams within Obra Real Estate and the broader Obra Capital platform
Qualifications & Requirements
Minimum of 2 years of relevant experience in commercial real estate, real estate lending, investment banking, private credit, or finance
Bachelor’s degree from a top‑50 university (real estate, finance, economics, or related field preferred)
Candidates local to Chicago strongly preferred
Strong financial modeling and analytical skills with the ability to draw independent conclusions
Proficiency in Microsoft Excel, PowerPoint, and Word
Strong written and verbal communication skills
High level of attention to detail, organization, and accountability
Entrepreneurial mindset with a strong desire to help build and grow a platform
In‑office role, 5 days per week, at ORE’s downtown Chicago office
Occasional travel for site visits and industry conferences
The expected base salary range for this role is outlined below. In addition to the base salary, total compensation may include a discretionary bonus based on performance. This range reflects a variety of factors, including years of relevant experience, education, and other qualifications pertinent to the position.
$70,000 - $100,000
The firm also offers robust Benefits offerings which include Comprehensive Medical/Rx, Dental and Vision plans; 401(k) program with company match; Flexible Savings Accounts (FSA); Healthcare Savings Accounts (HSA) with company contribution; Basic and Voluntary Life Insurance; Long-Term Disability (LTD) and Short-Term Disability (STD) insurance; and Commuter Benefits plan. In addition all employees of Obra are provided with a daily lunch stipend.
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