Property Specialist - Scattered Sites (5TM)

Location & Salary Location: Chicago, IL (Multi-Site) Reports To: Portfolio Manager Salary: $63,000 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 and a people-first leadership philosophy, we proudly serve communities with care, excellence, and integrity. About the Role The Property Specialist - Scattered Sites is responsible for the full operational performance of an assigned multi-property portfolio, currently including Damon Centre Apartments, 5727, 5800, and Ada Throop Apartments. This role owns occupancy, compliance, resident relations, maintenance coordination, and financial accountability across all assigned sites. This is a field-based role that demands a high degree of independence, strong organizational discipline, and the owner-operator mindset that defines how Five T Management works. You will operate under the direction of the Portfolio Manager, but you will drive results at every site without needing constant direction. Key Responsibilities Own day-to-day operations across all assigned scattered site properties, including Damon Centre Apartments, 5727, 5800, and Ada Throop Apartments. Conduct regular site visits at each property; inspect conditions, document deficiencies, and take corrective action. Manage the full leasing cycle at every site in compliance with Tenant Selection Plans, applicable program requirements, and Fair Housing law. Maintain site waitlists accurately across all properties, with applicant decisions documented per regulatory requirements. Keep all assigned properties in full compliance with applicable programs including LIHTC, HOME, PRA, NSP, Project-Based Section 8, HUD, CHA, and Market Rate requirements. Maintain resident files in audit-ready condition at every site at all times. Coordinate work orders with maintenance staff and vendors across all sites for on-time, on-budget completion. Monitor site operating budgets at each property, track expenses against approved plans, and flag variances promptly. Manage rent collection proactively across the portfolio, pursue delinquent accounts, and achieve collection targets at each site. Build and sustain strong resident relationships through consistent, professional touchpoints at every property. Prepare and submit required reports; maintain accurate records in Yardi and AppFolio across all sites. Manage the logistical demands of a scattered portfolio, including efficient travel scheduling and site-specific recordkeeping. Qualifications Required: High school diploma or GED required; associate's or bachelor's degree in Business, Real Estate, or a related field preferred. Minimum 3 years of property management experience, including demonstrated experience managing multiple sites or a scattered site portfolio. Valid Illinois Leasing Agent License, or ability to obtain within 6 months of hire. Fair Housing certification required, or ability to obtain within 6 months of hire. Working knowledge of affordable housing programs including LIHTC, HOME, PRA, NSP, Project-Based Section 8, HUD, CHA, or Market Rate. Proficiency in Yardi or AppFolio property management software. Proficiency in Microsoft Office Suite (Word, Excel, Outlook). Valid driver's license and reliable personal vehicle required for regular travel between all assigned sites. Strong organizational and written/verbal communication skills. Ability to work independently, manage time effectively across multiple sites, and meet deadlines without direct supervision. Preferred: Certified Occupancy Specialist (COS) or Tax Credit Specialist (TCS) certification. Experience with REAC/NSPIRE inspections and inspection-readiness programs. Experience managing mixed-program properties across multiple regulatory programs simultaneously. Bilingual - English/Spanish preferred. Benefits Competitive compensation Medical, dental, and vision insurance 401(k) retirement plan Paid time off #J-18808-Ljbffr 5T Management