Acquisitions Associate at Fairlawn – Chicago, Illinois

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.

What will you do?

• 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

Why should you work here?

• Competitive Pay. We are ready to invest in you!
• Additional monthly or quarterly incentive pay for meeting goals and supporting property performance
• Medical, Dental, Vision, and Life Insurance to access care for positive health outcomes and your overall wellbeing
• Employee sponsored benefits including Short Term Disability, Life Insurance, Critical Illness, Accident, Flexible Spending, and H.S.A. Accounts to avoid costly medical expenses due to gaps and ensure that all your medical needs are met
• 401(k) Retirement Plan with Match to invest in your future wealth and retirement
• Paid Vacation, Sick Leave, and Holiday Pay to help you reset and come back rejuvenated and refreshed
• Company events to promote team cohesion
• Wellness Days to focus on being your best self. We want you to have time to disconnect and recharge in a way that works for you
• 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 to celebrate wins, issue solve and ensure you are set up for success. Plus, the process is rewarding, and the results are great for your career

Why should you work here?

• Competitive Pay. We are ready to invest in you!
• Additional monthly or quarterly incentive pay for meeting goals and supporting property performance
• Medical, Dental, Vision, and Life Insurance to access care for positive health outcomes and your overall wellbeing
• Employee sponsored benefits including Short Term Disability, Life Insurance, Critical Illness, Accident, Flexible Spending, and H.S.A. Accounts to avoid costly medical expenses due to gaps and ensure that all your medical needs are met
• 401(k) Retirement Plan with Match to invest in your future wealth and retirement
• Paid Vacation, Sick Leave, and Holiday Pay to help you reset and come back rejuvenated and refreshed
• Company events to promote team cohesion
• Wellness Days to focus on being your best self. We want you to have time to disconnect and recharge in a way that works for you
• 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 to celebrate wins, issue solve and ensure you are set up for success. Plus, the process is rewarding, and the results are great for your career

Who you are — We'd love to hear from you if you have the following:

• 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 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
• Strong communication skills with the ability to present and defend underwriting assumptions and investment recommendations to internal stakeholders and external capital partners
• Capable of managing multiple active deals simultaneously without sacrificing accuracy, depth, or attention to detail
• Ability to work against firm deadlines, including flexible or extended hours during periods of elevated deal activity
• Superior attention to detail, high energy, and a positive attitude
• Ability to give and receive real-time feedback

Fairlawn is a vertically integrated firm specializing in real estate investment, management, and development. Based in Chicago and Champaign, Illinois, we have a more than 10-year track record in value-add projects, development, student housing, and build-to-rent communities. With a portfolio of approximately 5,750 units and $900 million in assets under management, Fairlawn has established a strong presence across Illinois, Indiana, and Kentucky. We are actively expanding into additional Midwest markets.

We are seeking candidates who demonstrate a strong alignment with the requirements listed above. While meeting all qualifications is preferred, we understand that exceptional candidates may bring comparable experience and skills to the table including prior experience at Fairlawn. We value diversity of thought and experience, and we are committed to considering all applicants [internal and external] and to identifying and selecting the most qualified applicant for the role.

Depending on the role requirements, offers of employment may be contingent upon one or more of the following: employment history verification, criminal background check, motor vehicle record check, education verification, or credit check.

Our company uses the Entrepreneurial Operating System (EOS) to run and help grow our business – the tools from EOS contribute to finding the right people and putting them in the right roles, effectively solving issues as they arise, and building a culture of accountability. In short, it gets everyone on the same page and working toward the same goals. If you have an ownership mindset and take pride in all the details, joining our team may be perfect for you!

We are an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, national origin or ancestry, sex, age, physical or mental disability, veteran or military status, genetic information, sexual orientation, marital status, or any other characteristic protected by law.