Executive Python Financial Jobs in Chicago, IL (NOW HIRING)

Cabrera Capital Partners is a national real estate development and investment platform focused on disciplined growth through long-term relationships. We partner with institutional capital and local stakeholders to originate and execute real estate opportunities across diverse markets. Our platform-driven strategy spans multiple real estate sectors, and emphasizes fundamentals, alignment, and repeatability, delivering durable assets and sustainable value.

The Real Estate Financial Analyst is a core contributor to how we source, underwrite, and execute deals. You will work directly with senior leadership across the full transaction lifecycle, from initial market screening through investment committee approval and into asset management. The work is fast-moving, intellectually demanding, and consequential. Operates with a high degree of autonomy in financial analysis and deal support. Exercises judgment in underwriting assumptions, analytical framing, and investment recommendations provided to senior leadership. We are a small team, which means your output matters immediately and visibility is high. 

Underwriting & Financial Analysis:

• Build and own complex cash flow models across property types including industrial, multifamily, student housing, and mixed use
• Develop, review, and stress test operating pro formas and investment return models (IRR, equity multiple, cash on cash) across a range of capital structures
• Sensitize assumptions across key variables (e.g., rent growth, vacancy, cap rates, construction costs, financing terms) and translate outputs into relevant investment conclusions
• Support debt and equity structuring analysis, including joint venture and waterfall modeling

Market & Property Research:

• Conduct primary and secondary market research using institutional data platforms (e.g., CoStar, Green Street, MSCI, or equivalent), as well as site visits, broker conversations, and local market intelligence
• Synthesize research into clear written investment theses and underwriting memoranda with a defined point of view
• Track sector, submarket, and competitive trends and maintain comparable and benchmarking analyses

Deal Execution & Investment Process:

• Support transactions from initial screening through LOI, due diligence, and closing
• Prepare investment committee materials including executive summaries, underwriting exhibits, risk assessment, and recommendation frameworks
• Coordinate with third party consultants, brokers, lenders, and legal counsel throughout the diligence and closing process
• Maintain pipeline tracking, deal logs, and internal investment databases

Property / JV / Platform FP&A & Reporting:

• Support property and JV level financial performance analysis, connecting underwriting assumptions to actual and forecasted results
• Analyze and communicate deal cash flows and partner economics, clearly showing sources and uses of capital across CCP and its partners
• Prepare property, JV, and portfolio level reporting that explains performance, returns, and variance to plan for internal and external stakeholders

Presentation & Communication:

• Build polished, boardroom ready investment decks and IC approval materials
• Distill complex financial and market analysis into clear, decision oriented narratives for senior leadership and external stakeholders
• Support preparation of materials for LP reporting, investor communications, and capital raising initiatives as needed

Technical Skills:

• Advanced Excel required, including dynamic model building and the ability to build models from scratch
• PowerPoint fluency, with the ability to develop clear, well structured presentations that effectively communicate analysis and recommendations
• Ability to automate repetitive analytical tasks (Python, VBA, or equivalent) is a meaningful differentiator
• Actively uses AI tools to accelerate research, drafting, and analysis, thoughtfully balancing their use with independent thinking

Professional Qualities:

• Exercises sound judgment, with the ability to identify key insights, prioritize relevant information, and filter out noise in both data and discussions
• Strong written communication skills demonstrated through clear, analytical memos, emails, and presentation materials
• Resourceful and self directed, with a demonstrated ability to find answers independently
• Intellectual curiosity about markets, capital flows, and the drivers of real estate value
• Comfortable operating in ambiguous environments and building process where none exists
• Demonstrates persistence and follow through to bring work to completion without requiring close oversight

• Bachelor’s degree required in finance, real estate, economics, or a related analytical field 
• 2 to 4 years of experience at an institutional real estate firm (investor, owner, operator, developer, REPE, REIT, or institutional advisory) 
• Demonstrated experience owning financial models, not just populating templates 
• Exposure to multiple property types and full cycle transaction experience through closing strongly preferred 
• CFA candidacy, MSRE, or MBA a plus, but not required

We offer a competitive and well-rounded benefits package designed to support your health, well-being, and financial future:

• Medical, Dental & Vision Coverage
• Paid Time Off & Holidays
• 401(k) with Employer Match
• Profit Sharing Program
• Flexible Spending & Health Savings Accounts (FSA/HSA)
• Commuter Benefits (Pre-tax transit & parking)
• Short- & Long-Term Disability Coverage
• Life & AD&D Insurance Options
• Employee Assistance Program (EAP)
• Pet Care Discount Program