Current Openings
Job Title: Real Estate Financial Analyst
Start Date: Q1 2026
Location: Chicago
Supervisor’s Title: Managing Director
FLSA: Exempt (from overtime requirements)
JOB DESCRIPTION
Seeking a financial analyst to work alongside and support the banking team within a boutique investment bank with a focus on structured commercial real estate financing, including Credit Tenant Loans (CTLs). Analysts have the opportunity to work on commercial real estate debt transactions from start to finish, including creating marketing materials for prospective clients, conducting research, financial analysis, modeling, preparing offering memorandums for institutional investors and assisting with the closing process. See below for more details.
Key Job Responsibilities
35% Financial Analysis and Modeling – Assess the credit strength of tenants, including public and private companies and municipalities, which entails spreading financial statements and using a proprietary shadow rating model; model bond amortization schedules based on different debt structures; collect financial data from Bloomberg and evaluate corporate and government yield curves and spreads.
20% Due Diligence – Obtain and track information required to perform pertinent analysis and to compose transaction-related documents throughout the life cycle of a deal including information required for initial quotes, answering investor questions, and the closing & documentation process.
20% Draft Transaction-Related Documents – Help draft loan applications, term sheets, offering memorandums and distribution lists.
10% Prepare Client Proposals, Presentations and Other Marketing Materials – Assist with creating tailored pitch books and presentations for prospective clients; create and update firm marketing materials and periodic business updates; prepare monthly credit rating updates.
10% Lease Review – Read and review commercial real estate leases to assess transaction viability and conduct financial modeling based on the terms and economics of the lease.
5% Research – Research specific tenant companies and their sector / industry and the capital markets and real estate market in general.
Qualifications (Preferred)
• Strong analytical, mathematical, writing and computer skills.
• Clear and effective communicator; takes responsibility for understanding others.
• Solid working knowledge of financial statements and accounting.
• Computer proficient (Excel, Word, PowerPoint, Bloomberg, CoStar).
• Bachelor’s degree required, concentration in finance or accounting preferred.
• One to three years of financial industry experience with a focus on credit and/or real estate.
• SIE Exam, Series 79 and 63 licenses within six months of hiring.
Competencies
• Achieves results
• Thinks analytically
• Detail-oriented with a concern for quality
• Clear communicator
• Takes initiative
• Conducts oneself in a professional manner
• Ability to juggle multiple tasks at a time
COMPANY DESCRIPTION
Waterway Capital is a broker-dealer and investment bank providing customized financing solutions for developers and owners of commercial real estate. With decades of experience, the Waterway team has built a reputation for advancing the industry with innovative ideas. We pioneered the credit tenant loan (CTL) market and have expanded over the years to become a leader in lease-backed structured finance. Waterway is headquartered in Boston with an office in Chicago.
ABOUT THE TEAM
With experience in investment banking, commercial real estate banking and fixed income sales and trading, the Waterway team offers unmatched expertise, personal attention and a market-leading approach. The banking team focuses on originating and structuring creative debt capital solutions for commercial real estate owners, investors and developers. Product types include credit tenant loan (CTL) financing, sale-leaseback transactions and structured private placements including structured ground lease transactions.
TO APPLY, PLEASE SUBMIT YOUR NAME, CONTACT INFORMATION AND RESUME TO: CAREERS@WATERWAYCAP.COM