Family Self Sufficiency (FSS) Program Supervisor

Location: Chicago, IL

Reports To: Senior Director of Operations

Role Type: Part-Time

Compensation: $40,000 per year

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. Through our IMPACT program, we go beyond housing to connect residents with the tools, resources, and support they need to build long-term economic stability. We proudly serve communities with care, excellence, and integrity.

About the Role

The IMPACT Program Supervisor leads the day-to-day operations of Five T Management’s Family Self-Sufficiency (FSS) program across designated properties in Chicago. This is a supervisory role with direct oversight of two IMPACT Coordinators and full accountability for program performance, HUD compliance, resident engagement, escrow management, and outcome reporting.

This position is primarily office-based with regular travel to properties across our portfolio. Evening or weekend availability may be required for community outreach activities. The ideal candidate is an experienced FSS professional who leads with a coaching mindset, holds themselves and their team to a high standard, and genuinely believes that stable housing is just the beginning of what a community can offer its residents.

Key Responsibilities

• Supervise two IMPACT Coordinators through structured one-on-ones, case reviews, and reflective supervision grounded in trauma-informed and motivational interviewing practices.
• Oversee the accurate and timely completion of Individual Training and Services Plans (ITSPs) and Contracts of Participation (CoPs) in compliance with HUD FSS Final Rule requirements.
• Monitor program performance metrics including enrollment, retention, goal progression, and escrow accumulation; use data to strengthen service design and staff coaching.
• Manage escrow calculations, OARQ submissions, interim and forfeited escrow disbursements, and all related documentation in full compliance with HUD policy and 5T accounting standards.
• Develop and execute quarterly outreach strategies to drive enrollment across all eligible properties; lead motivational screening and resident selection with professionalism and cultural sensitivity.
• Serve as the escalation point for complex resident concerns, case planning challenges, and participant disputes.
• Ensure all program activities comply with HUD FSS regulations, 24 CFR Part 984, and the HUD-approved Action Plan; maintain standard operating procedures and keep staff trained on current requirements.
• Submit required HUD reports, quarterly escrow statements, and performance dashboards accurately and on schedule.
• Lead quarterly Program Coordinating Committee (PCC) meetings and cultivate relationships with community partners including workforce agencies, childcare providers, educational institutions, and financial empowerment resources.
• Maintain audit-ready participant files, Yardi documentation, and program records at all times.
• Represent Five T Management professionally in external partner meetings, HUD reviews, and community settings.

Qualifications

• Minimum of two years of experience in HUD Family Self-Sufficiency (FSS) program administration required.
• Bachelor’s degree in Human Services, Public Administration, Urban Studies, or a related field preferred; Associate’s degree with four or more years of directly relevant experience will be considered.
• Prior supervisory or team leadership experience preferred.
• Demonstrated knowledge of HUD FSS regulations, 24 CFR Part 984, escrow account management, and supportive service coordination.
• Proficiency in Yardi Voyager, Microsoft Excel, and cloud-based document management systems.
• Strong written and verbal communication skills; ability to present data clearly to internal leadership and external stakeholders.
• Experience managing FSS programs in a multifamily affordable housing portfolio preferred.
• Familiarity with CHA, LIHTC, HUD Section 8, and other layered affordable housing program requirements is a plus.
• Certification in motivational interviewing, trauma-informed care, or a related coaching framework preferred.
• Bilingual capability in Spanish is a plus.

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.

Compensation: $40,000 per year.

Please note: This is a part-time position. Benefits including medical, dental, vision, 401(k), and paid time off are not included with this role.

Apply today and help us build stronger communities, one resident at a time.

Five T Management is an Equal Opportunity Employer. We do not discriminate on the basis of race, color, religion, national origin, sex, sexual orientation, age, disability, military or veteran status, or any other status protected by law.