Midwest Acquisitions Associate: AI-Driven Underwriting

Fairlawn; Chicago (IL); On-site; USD 90,000 - 120,000; Full time

Benefits offered by this job

Competitive pay

Annual bonus opportunities

Medical, dental, vision insurance

401(k) with company match

Paid vacation & holidays

Team events

Job summary

Fairlawn in Chicago, IL is seeking a detail-oriented Acquisitions Associate to join our growing team. You will produce institutional-quality underwriting for a robust pipeline of multifamily and student housing opportunities, building models from scratch and leveraging AI to improve accuracy and efficiency.

Based in Chicago, you will work alongside the Director of Acquisitions, manage end-to-end underwriting from screening through closing, and translate complex analyses into compelling

Qualifications

• Bachelor's degree in a related field (real estate, finance, accounting, business)
• Strong experience underwriting commercial real estate acquisitions
• Proven ability to build complex financial models from scratch
• Experience with CoStar, Yardi, AppFolio, Argus Enterprise
• Advanced Microsoft Excel and PowerPoint skills
• Interest in leveraging AI to enhance underwriting workflows

Responsibilities

• Own end-to-end underwriting across a robust deal pipeline from initial screening to closing
• Build, maintain, and stress-test financial models; manage model structure and assumptions
• Conduct market research, submarket analysis, and identify capex requirements to optimize asset performance
• Prepare investment memoranda and IC memos; present to internal committees and external partners
• Collaborate with Director of Acquisitions and cross-functional teams; support deal execution and process improvements
• Champion integration of AI tools into underwriting workflows

Education

Bachelor's degree in real estate, finance, accounting, business

Tools

CoStar

Yardi

AppFolio

Argus Enterprise

Excel (advanced)

PowerPoint

Job description

Fairlawn in Chicago, IL is seeking a detail-oriented Acquisitions Associate to join our growing team. You will produce institutional-quality underwriting for a robust pipeline of multifamily and student housing opportunities, building models from scratch and leveraging AI to improve accuracy and efficiency.

Based in Chicago, you will work alongside the Director of Acquisitions, manage end-to-end underwriting from screening through closing, and translate complex analyses into compelling