Leasing Advisor
CYM Living, Chicago, IL, United States
CYM Living - Where caring meets innovation. We are a national real estate firm with corporate headquarters in Chicago, IL, Indianapolis, IN and just outside of New York City. Our mission is to provide our residents with an exceptional living experience, nurture a culture of community, and empower growth from within. As a vertically integrated firm, we lead with operations by taking a hands‑on approach to real estate investment and property management, accomplishing our mission by incorporating data and technology with hyperlocal customer service to all units.
CYM Living is seeking a highly organized, customer‑focused Area Leasing Advisor to support leasing operations across a scattered‑site portfolio. This role serves as the primary human support contact when Leasing AI (Elise/Stella) escalates conversations that require judgment, empathy, or real‑time decision‑making. In addition to managing AI‑escalated prospect and resident communications, this role is directly responsible for leasing and supporting apartments assigned to the Zone Office portfolio, including units attached to the advisor’s home office. This position plays a critical role in increasing lead conversion, reducing dropped prospects, strengthening resident retention, and ensuring seamless coordination between AI systems, onsite teams, and management.
Requirements
Leasing, sales, or customer service experience
Strong written and verbal communication skills
Comfortable working in structured CRM workflows
Ability to manage high task volume and prioritize effectively
Highly organized and detail‑oriented
Calm, professional, and solution‑focused under pressure
Experience with Elise CRM and AppFolio preferred
Key Responsibilities Prospect Relations & AI Escalation Support
Act as the first human point of contact when Leasing AI escalates tasks due to:
Complex prospect questions
Requests for a live agent
Urgent or time‑sensitive leasing situations
Monitor and prioritize escalations within Elise CRM daily
Respond to prospect communications via:
Text
AI‑routed phone calls
Call‑back requests
Maintain strong knowledge of:
Pricing and availability
Property features and locations
Leasing policies (application fees, move‑in costs, pet policies, etc.)
Application requirements and approval process
Send applications and guide prospects through next steps
Monitor daily tour schedules and resolve scheduling conflicts
Serve as backup scheduling coordinator for Stella by reviewing calendars and confirming tours
Resident Relations & Retention Support
New move‑in follow‑up phone calls
Work order satisfaction phone calls
Renewal reminders
Delinquency calls
Resident satisfaction surveys
Delivering resident notices and 5‑day letters
Entering and tracking work orders
Handling light maintenance‑related questions
Responding to general resident inquiries
Escalating complex issues to Property Managers
Application, Move‑In & Pre‑Resident Coordination
Serve as the primary human contact once a prospect enters the approval stage
Confirm lease execution prior to move‑in
Ensure residents understand and acknowledge move‑in costs
Clearly communicate expectations and next steps
Track and manage Move‑In Inspection Forms
Upload completed documentation into AppFolio
Conduct renewal outreach for upcoming lease expirations
Escalate concerns appropriately
(This role does not generate renewal offers or negotiate lease terms.)
Media & Visual Leasing Support
Upload and maintain unit and property media in AppFolio:
Photos
Floorplans
Videos
Ensure media is accurate and up to date
Share approved visuals with prospects to support leasing conversations
Coordinate with onsite teams when updated media is needed
Reporting & Operational Support
Complete and submit Daily and Weekly Leasing Reports
Maintain ongoing communication with onsite leasing teams regarding:
Daily schedules
Tour confirmations
AI escalations
Scheduling changes
Provide administrative support during high‑volume periods
Leasing & Portfolio Responsibility (Home Office Assigned Units)
Managing all leasing activity for assigned units from inquiry to move‑in
Conducting virtual and/or in‑person tours (as applicable)
Following up with prospects and nurturing leads
Sending applications and guiding prospects through the approval process
Monitoring pricing, availability, and specials
Ensuring accurate listing information across websites and ILS platforms
Collaborating with onsite teams to prepare units for showings and move‑ins
Supporting occupancy goals and leasing performance targets
Benefits
Competitive base salary
Leasing bonuses and performance incentives
Full health benefits
Life insurance coverage
Paid Time Off (PTO)
Paid sick leave
Rotating weekly schedules to support work‑life balance
A supportive, collaborative, and unmatched company culture
We are committed to building a workplace where high performance, accountability, and team support coexist.
Equal Opportunity Employer CYM Living is an Equal Opportunity Employer. We are committed to creating a diverse and inclusive workplace and do not discriminate on the basis of race, color, religion, sex, gender identity, sexual orientation, national origin, age, disability, veteran status, genetic information, or any other protected characteristic in accordance with applicable federal, state, and local laws. We believe diversity strengthens our organization and enhances the communities we serve.
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CYM Living is seeking a highly organized, customer‑focused Area Leasing Advisor to support leasing operations across a scattered‑site portfolio. This role serves as the primary human support contact when Leasing AI (Elise/Stella) escalates conversations that require judgment, empathy, or real‑time decision‑making. In addition to managing AI‑escalated prospect and resident communications, this role is directly responsible for leasing and supporting apartments assigned to the Zone Office portfolio, including units attached to the advisor’s home office. This position plays a critical role in increasing lead conversion, reducing dropped prospects, strengthening resident retention, and ensuring seamless coordination between AI systems, onsite teams, and management.
Requirements
Leasing, sales, or customer service experience
Strong written and verbal communication skills
Comfortable working in structured CRM workflows
Ability to manage high task volume and prioritize effectively
Highly organized and detail‑oriented
Calm, professional, and solution‑focused under pressure
Experience with Elise CRM and AppFolio preferred
Key Responsibilities Prospect Relations & AI Escalation Support
Act as the first human point of contact when Leasing AI escalates tasks due to:
Complex prospect questions
Requests for a live agent
Urgent or time‑sensitive leasing situations
Monitor and prioritize escalations within Elise CRM daily
Respond to prospect communications via:
Text
AI‑routed phone calls
Call‑back requests
Maintain strong knowledge of:
Pricing and availability
Property features and locations
Leasing policies (application fees, move‑in costs, pet policies, etc.)
Application requirements and approval process
Send applications and guide prospects through next steps
Monitor daily tour schedules and resolve scheduling conflicts
Serve as backup scheduling coordinator for Stella by reviewing calendars and confirming tours
Resident Relations & Retention Support
New move‑in follow‑up phone calls
Work order satisfaction phone calls
Renewal reminders
Delinquency calls
Resident satisfaction surveys
Delivering resident notices and 5‑day letters
Entering and tracking work orders
Handling light maintenance‑related questions
Responding to general resident inquiries
Escalating complex issues to Property Managers
Application, Move‑In & Pre‑Resident Coordination
Serve as the primary human contact once a prospect enters the approval stage
Confirm lease execution prior to move‑in
Ensure residents understand and acknowledge move‑in costs
Clearly communicate expectations and next steps
Track and manage Move‑In Inspection Forms
Upload completed documentation into AppFolio
Conduct renewal outreach for upcoming lease expirations
Escalate concerns appropriately
(This role does not generate renewal offers or negotiate lease terms.)
Media & Visual Leasing Support
Upload and maintain unit and property media in AppFolio:
Photos
Floorplans
Videos
Ensure media is accurate and up to date
Share approved visuals with prospects to support leasing conversations
Coordinate with onsite teams when updated media is needed
Reporting & Operational Support
Complete and submit Daily and Weekly Leasing Reports
Maintain ongoing communication with onsite leasing teams regarding:
Daily schedules
Tour confirmations
AI escalations
Scheduling changes
Provide administrative support during high‑volume periods
Leasing & Portfolio Responsibility (Home Office Assigned Units)
Managing all leasing activity for assigned units from inquiry to move‑in
Conducting virtual and/or in‑person tours (as applicable)
Following up with prospects and nurturing leads
Sending applications and guiding prospects through the approval process
Monitoring pricing, availability, and specials
Ensuring accurate listing information across websites and ILS platforms
Collaborating with onsite teams to prepare units for showings and move‑ins
Supporting occupancy goals and leasing performance targets
Benefits
Competitive base salary
Leasing bonuses and performance incentives
Full health benefits
Life insurance coverage
Paid Time Off (PTO)
Paid sick leave
Rotating weekly schedules to support work‑life balance
A supportive, collaborative, and unmatched company culture
We are committed to building a workplace where high performance, accountability, and team support coexist.
Equal Opportunity Employer CYM Living is an Equal Opportunity Employer. We are committed to creating a diverse and inclusive workplace and do not discriminate on the basis of race, color, religion, sex, gender identity, sexual orientation, national origin, age, disability, veteran status, genetic information, or any other protected characteristic in accordance with applicable federal, state, and local laws. We believe diversity strengthens our organization and enhances the communities we serve.
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