Assistant Property Manager

📍 Park City, IL | 🕒 Full-Time | 💰 $50,000–$60,000

RTO Property is a vertically integrated real estate investment, development, asset management, and property management company in Park City, Illinois. We own and manage a growing portfolio of 300 residential units and professionally operated short-term vacation rentals throughout the Chicagoland area.

Our team oversees every aspect of property operations—from acquisitions and leasing to maintenance, renovations, hospitality operations, and resident services. We are committed to delivering exceptional experiences for our residents, guests, investors, and property owners while creating long-term value through operational excellence.

As our company continues to grow, we're seeking an organized, detail-oriented, and customer-focused Assistant Property Manager to join our team.

The Assistant Property Manager supports the daily operations of both long-term residential communities and professionally managed short-term vacation rentals. Working closely with the Property Management team, you'll help ensure properties are well maintained, residents and guests receive exceptional service, leasing operations run smoothly, and maintenance requests are handled efficiently.

This is an excellent opportunity for someone looking to build a long-term career in property management, real estate operations, hospitality, or asset management.

Responsibilities:

Property Operations

• Assist with the day-to-day management of residential and short-term rental properties.
• Conduct routine property inspections and identify maintenance or operational needs.
• Coordinate move-ins, move-outs, turnovers, and property readiness.
• Ensure properties meet company quality standards and are guest-ready.
• Maintain organized property records and documentation.

Resident & Guest Relations

• Serve as a primary point of contact for residents, guests, property owners, and prospective tenants.
• Respond promptly and professionally to inquiries, maintenance requests, and concerns.
• Coordinate guest arrivals, departures, and special requests.
• Build positive relationships through exceptional customer service.
• Assist with conflict resolution and issue management.

Maintenance & Vendor Coordination

• Receive and prioritize maintenance requests.
• Schedule vendors, contractors, cleaners, and maintenance technicians.
• Follow up to ensure repairs are completed accurately and on time.
• Assist with preventative maintenance scheduling.
• Obtain vendor quotes and coordinate small projects.

Leasing & Property Administration

• Prepare leases, renewals, notices, and rental agreements.
• Assist with tenant screening and leasing administration.
• Coordinate lease renewals and monitor upcoming expirations.
• Manage reservation calendars across vacation rental platforms.
• Assist with pricing updates and listing accuracy.

Housekeeping & Turnovers

• Schedule cleaning teams between guest stays.
• Coordinate inspections after cleanings.
• Ensure homes are fully stocked with guest supplies and amenities.
• Assist with furnishing, inventory management, and seasonal property preparation.

Administrative & Financial Support

• Process invoices and assist with vendor payments.
• Assist with rent collection tracking and guest payment reconciliation.
• Maintain accurate information within AppFolio and other management software.
• Prepare occupancy, maintenance, and property performance reports.
• Support the Property Manager with special projects and operational initiatives.

Preferred Qualifications:

• 1–3 years of experience in property management, residential leasing, hospitality, real estate operations, or customer service
• Experience supporting short-term rentals (Airbnb, VRBO, etc.) is a plus
• Experience with AppFolio, Hostaway, Airbnb, VRBO, Yardi, or similar software preferred
• Knowledge of leasing, resident relations, maintenance coordination, and vendor management
• Strong communication and customer service skills
• Excellent organizational skills and attention to detail
• Proficient in Microsoft Office and Google Workspace
• Basic understanding of rent collections, invoices, and reporting preferred
• Valid driver's license and reliable transportation
• High school diploma required; additional education in business, hospitality, or real estate is a plus

Work Schedule

• Full-time, Monday–Friday
• On-site at our Park City, IL
• Regular travel to company properties throughout Lake County (mainly Libertyville and Waukegan)
• Summer Fridays: Office closes at 2:00 PM

Compensation & Benefits

• $50,000–$60,000 annual salary (based on experience)
• 15 days of Paid Time Off (PTO), plus company holidays
• 100% employer-paid Blue Cross Blue Shield medical insurance
• Employer-sponsored dental insurance
• 401(k) with company match up to 3%
• Professional development and career growth opportunities

Why join RTO Property?

At RTO Property, you'll become part of a collaborative, entrepreneurial team that values initiative, accountability, and continuous improvement. You'll gain hands-on experience across property management, leasing, hospitality, maintenance coordination, and real estate operations while helping manage a diverse portfolio of residential communities and professionally managed vacation rentals.

If you're looking for a role where you can make an impact and grow with an expanding company, we'd love to hear from you.