Compliance Specialist

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 - Conduct audits of move-in, recertification, interim, and move-out tenant files to ensure compliance with LIHTC, HUD, Section 8, PRAC, PRA, CHA, IHDA, DOH, HOME, and other applicable programs. - Prepare detailed audit reports with clear findings and corrective action recommendations; track resolutions through completion. - Review lease agreements, income documentation, and eligibility certifications for accuracy and completeness. - Ensure EIV reports are generated, reviewed, and documented in accordance with HUD guidelines; maintain site binders and compliance records in audit-ready condition. - Conduct monthly site audits on an established cadence; confirm that audit benchmarks are maintained and met. - Provide compliance coaching and follow-up support to property management staff; facilitate communication around file deficiencies and corrective timelines. - Support lease-ups and site onboarding, including managing electronic application intake, waiting list logging, and weekly progress updates to the Compliance Officer. - Assist with updates and revisions to compliance forms and documentation as needed. - Stay current on regulatory changes to LIHTC, HUD, HOME, and other program requirements; maintain active certifications and designations. - Escalate compliance risks early with recommended solutions to protect asset value and resident integrity. Qualifications - Minimum of 2 years of experience in affordable housing compliance, property management, or auditing; LIHTC, IHDA, DOH, Section 8, or HUD experience strongly preferred. - One or more industry designations required (e.g., Blended Occupancy Specialist, LIHTC Specialist, Certified Occupancy Specialist). - Strong working knowledge of HUD 4350, IRS Tax Code Section 42, Fair Housing laws, and related program regulations. - Proficiency in Microsoft Word, Excel, and Outlook; Yardi or similar property management software required. - High school diploma or equivalent required; two or more years of college, vocational training, or equivalent specialized experience preferred. - Ability to communicate audit findings clearly in writing and verbally. - Strong organizational skills and ability to manage multiple priorities independently. - Five or more years of experience with annual recertifications and knowledge of the Chicagoland housing market are a plus. Why Work With Us At Five T Management, our success…