Real Estate Business Strategy Analyst - Multifamily

Business Strategy Analyst, Multifamily Assets

Location: Chicago, IL (Hybrid)

Company: Skybox Capital

Team: Investments

Reports To: VP of Investments

Skybox Capital, a family office and private equity firm, is seeking a highly analytical Real Estate Strategy Analyst with experience in financial reporting, forecasting, and performance analysis. This role will focus on supporting the growth of the multifamily property management business.

The ideal candidate has an interest in real estate and an excellent grasp of fundamental accounting principles and financial review (income statements, balance sheets, cash flow). This role is designed for a detail-driven individual who enjoys digging into numbers, understanding operational drivers, and helping leadership make data-driven decisions. This is a high visibility role in a quickly growing organization and unique opportunity to work directly with senior leadership team members.

• Financial Review & Reporting
• Analyze monthly, quarterly, and annual financial statements, with a focus on identifying potential areas of opportunity for the business.
• Prepare financial dashboards and reporting packages.
• Identify trends, operational drivers, and risks across the property portfolio.
• Assist in forecasting the performance of the property management company, including staffing, maintenance, G&A expenses, and portfolio-wide operational impacts.
• System & Data Management
• Work with accounting, property management and business intelligence systems to extract, validate, and interpret financial and operational data.
• Ensure accuracy of data feeds and reporting outputs across systems and spreadsheets.
• Implement process improvements to enhance reporting accuracy, speed, and clarity.
• Cross-Functional Collaboration
• Collaborate closely with accounting/finance teams and operations teams to execute leadership strategy.
• Support underwriting and scenario modeling for strategic growth opportunities, including M&A.
• Participate in quarterly business reviews and investment performance meetings.

• Bachelor’s degree in Finance, Accounting, Economics, or related field.
• 1+ years of FP&A, finance, or consulting experience.
• Strong understanding of income statements, balance sheets, cash flow statements, and GAAP principles.
• Strong Excel modeling skills (index/match, pivot tables, forecasting, scenario modeling).
• Ability to interpret financial results and explain operational drivers clearly.
• Detail-oriented, organized, and able to work in a fast-paced investment environment.

• Experience working in a consulting, investment banking, or FP&A setting.
• Exposure to real estate property management.
• Ability to build dashboards or reports in BI tools (Power BI preferred).

• Work directly with investment team and company leadership in a lean, high-impact environment.
• Gain deep exposure to real estate operations, property management strategy, and portfolio company performance.
• Competitive compensation, bonus opportunity, and career development within a quickly growing firm.
• A hands-on role where your analysis directly influences decisions on capital deployment, strategy, and investment oversight.