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Ensure portfolio-wide compliance with federal, state, and local affordable housing regulations through rigorous file audits and eligibility verification. Provide coaching and guidance to site teams to resolve deficiencies and maintain audit-ready records.
Requires at least 2 years of affordable housing compliance experience and at least one industry designation such as COS or LIHTC Specialist. Proficiency in Yardi and a strong understanding of HUD 4350 and IRS Tax Code Section 42 are required.
Location: Chicago, IL (Portfolio-Wide)
Reports To: Compliance Officer
Salary Range: $55,000 – $60,000
Who We Are
Five T Management is a values-driven property management and development company based on Chicago’s South Side. We develop, own, and manage affordable apartment homes that residents are proud to call home. Founded on the belief that the vibrancy of a community can be restored, we are committed to delivering high-quality housing while creating an engaged work culture where our team members can contribute, learn, and thrive.
We manage each property like it’s our own, stewarding both our residents’ living experience and our owners’ investment. With deep expertise in affordable housing compliance across LIHTC, HUD, Section 8, CHA, IHDA, and other programs, we proudly serve communities with care, excellence, and integrity.
About the Role
The Compliance Specialist is responsible for ensuring properties across our portfolio remain in full compliance with federal, state, and local affordable housing regulations. Working under the direction of the Compliance Officer, this role conducts file audits, verifies eligibility documentation, prepares compliance reports, and provides coaching and guidance to site teams.
This position is primarily office-based with regular site visits across our Chicago-area portfolio. The ideal candidate is detail-oriented, self-directed, and deeply knowledgeable about affordable housing compliance. They bring a coaching mindset to their work, helping site staff grow their compliance skills rather than just identifying problems.
Key Responsibilities
Qualifications
Why Work With Us
At Five T Management, our success starts with our people. We foster a collaborative, high-performance culture where every team member is empowered to contribute, learn, and grow. We take pride in managing each property like it’s our own and making a meaningful impact in the communities we serve.
We offer:
Apply today and help us build stronger communities, one resident at a time.
We manage each property like it's our own!
5T Management was established in 2000. We started with our own portfolio of properties to fulfill a need for quality, safe and affordable housing for the communities we serve. Since 2000, we have grown based on our reputation of taking an innovative approach to property management. We are sought out because we are property owners ourselves and treat each property we manage as if it were our own! 5T is motivated by a belief that the vibrancy of a community can be restored. We believe in "getting it done", making the communities we serve better, providing excellent tenant relations, managing the asset for our owners cost effectively and efficiently and providing an environment where our employees can learn and thrive. We believe in resident relations, quality housing, safety, innovation, financial management and employee development. Our strengths are Yardi Voyager 7S, solid business practices, property management, property ownership, real estate development, accounting, compliance, operations, leadership development, customer relations and construction management. 5T Management's experience encompasses managing Market Rate, Low Income, LIHTC, PRA, NSP and Project Based Section 8 Rental units throughout Chicago's south and west sides. 5T's units bring stability to their respective Chicago neighborhoods and make their communities better by providing safe, clean and quality housing to residents. 5T has extensive relationships with the City of Chicago's Troubled Building Initiative, City Alderman, City of Chicago Police Department (CAPS), Department of Housing, Department of Buildings, Department of Law, Department of Administrative Hearings, Department of Planning and Development, Department of Human Services, Department of Water Management and the federal Department of Housing and Urban Development.
Offices: 647 E 75th St, Chicago, Illinois, US
Based on 3256 listings with disclosed salaries, most finance & accounting jobs in Chicago, IL pay between $65k–$181k per year. Individual offers vary with seniority, company size, and specialization.
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