Leasing Advisor
Cymliving, Chicago, IL, United States
Overview
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. 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, or urgent/time-sensitive leasing situations Monitor and prioritize escalations within Elise CRM daily Respond to prospect communications via text, AI-routed phone calls, and call-back requests Maintain knowledge of pricing and availability, property features and locations, leasing policies (application fees, move-in costs, pet policies, etc.), and the application requirements/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 Support resident satisfaction and retention through proactive communication and follow-up New move-in follow-up calls, work order satisfaction calls, renewal reminders, delinquency calls, and resident satisfaction surveys Deliver resident notices and 5-day letters; enter and track work orders; respond to general resident inquiries Escalate complex issues to Property Managers Deliver application, move-in, and pre-resident coordination as part of the process 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 Move-In Inspection Forms; upload documentation into AppFolio Conduct renewal outreach for upcoming lease expirations Escalate concerns appropriately 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, and scheduling changes Provide administrative support during high-volume periods Leasing & Portfolio Responsibility (Home Office Assigned Units) Directly lease apartments attached to the designated home office portfolio (inquiry to move-in) Conduct virtual and/or in-person tours as applicable Follow up with prospects and nurture leads; send applications and guide through approval Monitor pricing, availability, and specials; ensure accurate listing information across websites and ILS platforms Collaborate with onsite teams to prepare units for showings and move-ins; support occupancy goals and leasing performance targets This role carries direct accountability for leasing performance within the assigned portfolio. Qualifications
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 Benefits
Competitive base salary • Leasing bonuses and performance incentives Full health benefits Life insurance coverage PTO Paid sick leave Rotating weekly schedules to support work-life balance A supportive, collaborative, and unmatched company culture 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 - 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. 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, or urgent/time-sensitive leasing situations Monitor and prioritize escalations within Elise CRM daily Respond to prospect communications via text, AI-routed phone calls, and call-back requests Maintain knowledge of pricing and availability, property features and locations, leasing policies (application fees, move-in costs, pet policies, etc.), and the application requirements/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 Support resident satisfaction and retention through proactive communication and follow-up New move-in follow-up calls, work order satisfaction calls, renewal reminders, delinquency calls, and resident satisfaction surveys Deliver resident notices and 5-day letters; enter and track work orders; respond to general resident inquiries Escalate complex issues to Property Managers Deliver application, move-in, and pre-resident coordination as part of the process 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 Move-In Inspection Forms; upload documentation into AppFolio Conduct renewal outreach for upcoming lease expirations Escalate concerns appropriately 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, and scheduling changes Provide administrative support during high-volume periods Leasing & Portfolio Responsibility (Home Office Assigned Units) Directly lease apartments attached to the designated home office portfolio (inquiry to move-in) Conduct virtual and/or in-person tours as applicable Follow up with prospects and nurture leads; send applications and guide through approval Monitor pricing, availability, and specials; ensure accurate listing information across websites and ILS platforms Collaborate with onsite teams to prepare units for showings and move-ins; support occupancy goals and leasing performance targets This role carries direct accountability for leasing performance within the assigned portfolio. Qualifications
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 Benefits
Competitive base salary • Leasing bonuses and performance incentives Full health benefits Life insurance coverage PTO Paid sick leave Rotating weekly schedules to support work-life balance A supportive, collaborative, and unmatched company culture 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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