Residential Portfolio – South Chicago (1099 Contractor Role)
Overview: We are looking for a proactive, inquisitive, and adaptable Assistant Property Manager (1099 Independent Contractor) to manage daily field operations and resident relations for our South Chicago residential portfolio. The role requires a firm yet humble demeanor, a desire to learn property management, and a willingness to perform occasional light maintenance tasks.
Key Responsibilities & Duties
- Field-Based Property Oversight: Conduct routine, move-in, move-out, and pre-inspection walkthroughs across the residential portfolio to ensure buildings meet safety and operational standards.
- Resident & Tenant Relations: Act as a primary point of contact for tenant inquiries, complaints, and lease enforcement with a firm yet empathetic communication style.
- Leasing Support & Showings: Coordinate and conduct vacant unit showings for prospective tenants, answer leasing inquiries, and assist with the collection of application materials.
- Maintenance & Light Handyman Coordination: Troubleshoot basic tenant maintenance requests on-site. The incumbent must be open to directly performing minor, simple maintenance tasks (e.g., changing lightbulbs, replacing smoke detector batteries, or basic fixture tightening) before escalating to specialized contractors.
- Vendor Escorting & Monitoring: Coordinate access for utility workers, inspectors, and specialized maintenance contractors, verifying that outsourced work is completed satisfactorily.
- Rent Collection Support: Assist management with local notices delivery, rent drop-offs, or following up on outstanding accounts within the assigned geographic zone.
- Local Proximity Response: Leverage your residency in or near the South Chicago area to respond promptly to localized property needs, sudden notice postings, or site walk-through requests.
- Administrative Reporting: Maintain clear, organized logs of property conditions, upload digital inspection photos, and provide concise daily or weekly updates to the remote management team.
Job Requirements & Qualifications
- Ideally a resident of the South Chicago area, or explicitly reside within the broader city limits of Chicago with an intimate knowledge of the local neighborhoods.
- Must have a valid U.S. Driver’s License, a reliable and functioning personal vehicle, and active auto insurance. Daily travel between localized portfolio sites is mandatory.
- Must own a working smartphone with an active data plan.
- An inquisitive nature with an eagerness to learn real estate operations. You must display a balanced personality—firm when enforcing policies, yet grounded in humility when interacting with tenants and team members.
- The selected final candidate will be required to successfully pass a comprehensive background and criminal check prior to formal contract signing.
Compensation & Contractor Fee
This is a 1099 Independent Contractor position. The contractor is responsible for providing their own vehicle, mobile phone, and tools for minor maintenance tasks. Compensation will be a flat, all-inclusive professional fee paid weekly with additional gas expenses reimbursement.
This position is also eligible for very attractive and uncapped Pay for Performance in the form of KPI-based incentives, which are paid on a monthly basis.
Total Weekly Contractor Fee: $900 per week
