Acquisitions Associate

Fairlawn Management • Chicago, IL

23h • Onsite

About The Position

Fairlawn is a vertically integrated investment, development, and management platform. Based in Chicago and Champaign, Illinois, we have a more than 10-year track record across two distinct verticals: student housing and middle market multifamily, where we deploy both value-add acquisition strategies and ground-up development. With a portfolio of approximately 6,000 units and approximately $1 billion in assets under management, Fairlawn has established a strong presence across Illinois, Indianapolis, and Kentucky. We are actively expanding into additional Midwest markets. The Opportunity We are seeking a detail-oriented Acquisitions Associate to join our growing team at Fairlawn. The ideal candidate will embody Fairlawn's core values: Be Kind, Own It, Be Flexible, and Always Improve. Are you a financial modeler at heart — someone who gets energized by working through a high volume of deals, builds airtight models from scratch, has a genuine passion for leveraging AI to elevate the quality and efficiency of their work, and can translate complex investment analysis into compelling narratives that drive decisions? If so, our Acquisitions Associate role may be the perfect fit. Based in Chicago, Illinois, this team member will serve as the analytical engine of our Acquisitions team, producing institutional-quality underwriting at scale across a robust pipeline of multifamily and student housing acquisitions and ground-up development opportunities across our growing Midwest portfolio. The Acquisitions Associate will work alongside our Director of Acquisitions and play a key role in Fairlawn's investment process from initial screening through closing.

Requirements

• Bachelor's degree in real estate, finance, accounting, business, or a related field
• Minimum of 3 years of experience underwriting and analyzing commercial real estate acquisitions, developments, and financings — with a demonstrated track record of institutional-quality work product across a high volume of deals; additional experience beyond 3 years is a plus
• A genuine passion for AI and a proven track record of using AI tools to enhance personal productivity and work product quality — and the drive and technical curiosity to build AI-assisted underwriting workflows and processes that benefit the broader team
• Proven ability to build complex, dynamic financial models entirely from scratch — not just populate or modify existing templates, but architect model logic, build flexible assumption drivers, and stress-test outputs with rigor and precision
• Deep experience underwriting both value-add multifamily acquisitions and ground-up development projects, including construction costs, development timelines, and lease-up assumptions
• Experience working on a transactional team with a proven track record of closing multifamily and/or student housing real estate investments
• Expert proficiency in Microsoft Excel — candidates should be comfortable with advanced functions, dynamic modeling structures, and building institutional-grade models without reliance on pre-built templates
• Experience with industry tools such as CoStar, Yardi, AppFolio, Argus Enterprise, etc.
• Expert with Microsoft PowerPoint with demonstrated ability to craft clear, compelling investment narratives and pitch materials for sophisticated internal and external audiences
• Ability to work independently with a high degree of ownership — comfortable making well-supported investment recommendations and drafting investment narratives with limited direction

Nice To Haves

• additional experience beyond 3 years is a plus
• prior experience at Fairlawn

Responsibilities

• Exemplify the core values of Be Kind, Be Flexible, Own It, and Always Improve
• Own the end-to-end underwriting process across a robust and active deal pipeline — from initial screening and deal evaluation through IC presentation and closing — with precision, depth, and conviction
• Build, maintain, and continuously improve financial models from scratch, including full ownership of Fairlawn's master underwriting template — architecting the model structure, stress-testing assumptions, enhancing functionality, and ensuring models reflect current market conditions and deal-specific nuances
• Complete advanced financial analysis and underwriting of multifamily and student housing acquisitions and ground-up development opportunities, including sensitivity analysis, scenario modeling, debt and equity structuring (capital stack structuring, loan sizing, return metrics including IRR, equity multiple, and cash-on-cash returns)
• Maintain responsibility for the quality and accuracy of all underwriting assumptions, including conducting market research, submarket analysis, and identifying necessary operational and capital expenditure requirements to enhance asset performance — and independently formulate recommendations on business plan, deal structure, and return optimization
• Champion the integration of AI tools into the underwriting workflow — not just as a personal productivity tool, but as an active builder of AI-assisted processes, templates, and systems that elevate the quality and efficiency of the broader acquisitions team
• Underwrite ground-up development projects including construction costs, development timelines, and lease-up assumptions, coordinating with asset management, property management, and construction management teams to validate and stress-test inputs
• Independently prepare investment pitch books and IC memos — translating complex underwriting into clear, compelling, and defensible investment narratives that will be presented to the internal Investment Committee and external capital partners by the Director of Acquisitions and senior leadership
• Support deal execution, from initial underwriting through closing, including coordination with internal and external partners
• Participate in process improvements initiatives and cross-functional projects as the team and portfolio grow
• Foster existing relationships with brokers, lenders, investors, consultants, sellers, and internal operational teams to assist in deal execution

Benefits

• Competitive Pay
• Additional monthly or quarterly incentive pay for meeting goals and supporting property performance
• Medical, Dental, Vision, and Life Insurance
• Employee sponsored benefits including Short Term Disability, Life Insurance, Critical Illness, Accident, Flexible Spending, and H.S.A. Accounts
• 401(k) Retirement Plan with Match
• Paid Vacation, Sick Leave, and Holiday Pay
• Company events
• Wellness Days
• The opportunity to work for a growing organization where you are valued and can have a direct impact
• Quarterly off-site meetings with your manager

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level