Hi there! I'm based in Winter Garden, Florida, where I live with my amazing 10-year-old son After growing up vacationing here, it was always a dream of mine to call this area home, and I'm grateful to now be living that dream every day Professionally, I have built my career around creating meaningful connections, leading teams, and delivering exceptional experiences Beyond my corporate background, I am a passionate advocate for maternal mental health, particularly supporting mothers through the postpartum journey, and have had the privilege of speaking on several panels to help raise awareness and encourage open conversations I'm also a licensed makeup artist, which allows me to express my creativity while helping others feel confident and empowered Whether I'm planning community events, leading a team, or simply connecting with people, I thrive on building relationships and creating welcoming environments where others feel valued I have always considered myself a natural leader with a genuine passion for people I pride myself on my work ethic, positive attitude, and ability to make others feel comfortable, supported, and seen I believe that strong relationships are the foundation of every successful team and community, and I strive to leave a positive impact everywhere I go
Haylee J Cunningham
Winter Garden,FL
Summary
Accomplished Property Management, Community Operations and Event planning professional leading residential communities, overseeing daily operations, and producing large-scale lifestyle programming and events. Proven success managing resident relations, vendor partnerships, operational logistics, leasing functions, cross-functional teams, and community engagement initiatives within luxury residential and apartment communities. Skilled at collaborating with HOA Boards, Food & Beverage, contractors, and internal departments to improve resident satisfaction, streamline operations, and execute high-impact community events ranging from intimate workshops to festivals serving more than 4,000 residents. Recognized for building strong stakeholder relationships, negotiating vendor contracts, managing budgets, and delivering exceptional customer experiences while maintaining operational excellence. Seeking a leadership role in event management, residential property management, or luxury resort-style communities where I can drive operational excellence, enhance resident experiences, and lead high-performing teams.
Overview
13
13
years of professional experience
1
1
Certification
Work History
Community & Lifestyle Director
KW Property Management
03.2026 - Current
- Developed and implemented community engagement programs to enhance resident satisfaction.
- Created and structured BEO's for each community or corporate event.
- Partnering and directing the onsite Food & Beverage team before, during and after each event, program or retreat.
- Collaborated with vendors to provide quality services and activities for community members.
- Mentored team members in event planning and execution, promoting best practices across departments to ensure event success.
- Recruited trained, and supervised a team of dedicated volunteers to assist in executing successful events.
- Served as a liaison between management staff, the Board of Directors and residents regarding communication about upcoming events or changes in scheduling or programming.
- Oversaw budgeting for lifestyle programs, ensuring cost-effective use of resources while maximizing value for residents.
Community Relations & Lifestyle Director
OnPlace LLC | Pulte Homes
01.2025 - 03.2026
- As a Lifestyle Director and Community Relations Director at a 55+ active adult residential community, I plan and execute engaging events and seminars to foster a vibrant, active lifestyle for over 1000 residents. I also serve as a liaison between the home builder, our client, and residents, ensuring smooth communication and a positive community experience during the ongoing construction phase.
- Served as the main POC for incoming residents, prospects and vendors
- Coordinated with vendors and suppliers to negotiate contracts and secure necessary resources for successful event execution
- Collaborated with cross-functional teams to develop event concepts and themes that aligned with client objectives
- Oversee the onsite Food & Beverage staff before, during and after all events. Processed BEOs and corresponding invoices
- Developed detailed event timelines, schedules, and production plans to ensure smooth operations during the entire event lifecycle
- Coordinated entertainment bookings such as live bands, DJs or performers aligning their schedules with the overall event program
- Managed multiple concurrent projects while adhering to strict deadlines and budgets
- Handled all rentals needed for each event
Community & Lifestyle Director
Castle Group Property Management | Pulte Homes
03.2025 - Current
- Coordinated lifestyle events, fostering a vibrant community atmosphere among residents.
- Established partnerships with local businesses to offer exclusive discounts and benefits to residents.
- Mentored team members in event planning and execution, promoting best practices across departments.
- Analyzed resident feedback to refine program offerings and increase participation rates effectively.
- Provided personalized experiences through one-on-one consultations assisting residents in finding suitable activities matching their personal interests.
- Increased community engagement by organizing various social, educational, and recreational activities for residents.
Community Association Manager
Castle Group Property Management | Pulte Homes
09.2023 - 03.2024
- Managed day-to-day operations of multiple community associations, ensuring compliance with regulations and standards.
- Coordinated maintenance and repair projects, enhancing community aesthetics and functionality.
- Developed and implemented community engagement programs to foster resident participation and satisfaction.
- Successfully hired and trained Management, Front Desk, Maintenance and Landscape Liasion staff for the property.
- Effectively communicated between residents, internal management, and the Developer (Pulte Homes) on a day to day basis as the community was deep in construction.
- Streamlined communication processes between residents and management through digital platforms.
- Conducted regular property inspections to identify maintenance needs and ensure safety compliance.
Assistant Property Manager
NM Residential
06.2022 - 09.2023
- Assistant Property Manager at the new 55+ Active Adult Community in Ocoee, Florida. Arya at Windermere houses approximately 148 units and five star amenities for our residents.
- Portray the property and amenities in a positive and upstanding fashion
- Reporting the property’s financial status, occupancy and expiring leases to property owners
- Maintain working knowledge of the property market and conduct weekly market surveys
- Negotiate leasing contracts to secure property occupation
- Facilitate housing repairs with tenants and maintenance staff
- Maintaining a positive resident retention rate and obtaining resident occupancy
- Investigating and resolving property complaints and rental violations
- Help and coordinate events for current and future residents (Le Wine + movie nights, Live Music, Chef Dinners)
Licensed Property Manager
Southcorp Properties
09.2018 - 12.2021
- Assistant Property Manager specializing in Multifamily Residential Property of approximately 300+ units. On-site and on call Manager.
- Directing the supervision of all leasing and maintenance staff on property.
- Screening applicants according to company policies. Credit reports, referrals, etc.
- Skilled with Yardi, Yardi Voyager, and RentCafe.
- Overseeing move in inspections per guidelines.
- Setting appointments, showings, and maintaining an exceptional occupancy rate each quarter.
- Rent collections, delinquencies, evictions.
- Assisting in handling the accounts payable to each phase of our property and inputting invoices correctly.
- Marketing for new tenants and potential vendors.
- Running our Social Media for marketing and/or presentation of our property.
- Oversaw tenant relations, addressing concerns promptly to enhance satisfaction and retention.
- Managed property operations, ensuring compliance with local regulations and organizational policies.
- Developed and implemented maintenance schedules, improving response times for service requests.
- Conducted regular property inspections, identifying areas for improvement and preventive maintenance needs.
- Conducted thorough property inspections regularly, ensuring adherence to safety standards and maintaining a well-maintained environment.
- Built rapport with tenants through regular communication and prompt resolution of concerns, fostering a positive living environment.
Assistant Branch Manager
Southern Management Corporation
04.2017 - 09.2018
- Assistant Branch Manager at a personal loan financial institution.
- Preparing office for future audits that might occur
- Led branch operations to ensure compliance with company policies and procedures.
- Evaluated loan applications to determine creditworthiness and risk levels.
- Streamlined loan processing workflows to enhance efficiency and reduce turnaround times.
- Mentored junior loan officers, providing guidance on best practices and industry standards.
- Conducted regular training sessions on updates in lending policies and procedures for staff development.
Licensed Pharmacy Technician
Rite Aid
03.2013 - 05.2016
- Assist pharmacist and fellow technicians in daily duties.
- Weekly inventory log.
- Corresponding between pharmacies and insurance companies on the patients behalf to ensure the best service.
- Dispensed medications accurately, ensuring compliance with pharmacy regulations and standards.
- Assisted pharmacists in managing inventory, reducing waste through effective stock control practices.
- Provided exceptional customer service, addressing inquiries and resolving issues promptly to enhance patient satisfaction.
- Mentored junior technicians, fostering skill development and promoting adherence to best practices in medication handling.
- Conducted medication therapy management consultations, ensuring proper patient education on drug usage and side effects.
Education
Accredited Property Manager - Real Estate
South Carolina Real Estate Commission
Greenville09-2018
Diploma
Blacksburg High School
Blacksburg, SC05-2012
Skills
- Problem-solving
- Banquet Orders
- Large Scale Corporate Events
- Large Scale Community Events
- Hospitality
- Accounts Receivable
- Payroll
- Lease Preparation
- Lease Renewals
- Contract Negotiation
- Team Leadership
- Yearly Community Programming
- Onsite Property Management
- SODAS
- Yardi Software
- Client Relationship Development
- Vendor Sourcing
- BEOs
- Vendor Negotiation
- Guest Management
- Microsoft Office Suite
- Food & Beverage Management
Certification
- Pharmacy Technician (Certification) 01/2013 - 03/2015 Penn Foster Career School
- Certified Property Manager
- Certified Apartment Manager
Interests
Timeline
Community & Lifestyle Director
KW Property Management
03.2026 - Current
Community & Lifestyle Director
Castle Group Property Management | Pulte Homes
03.2025 - Current
Community Relations & Lifestyle Director
OnPlace LLC | Pulte Homes
01.2025 - 03.2026
Community Association Manager
Castle Group Property Management | Pulte Homes
09.2023 - 03.2024
Assistant Property Manager
NM Residential
06.2022 - 09.2023
Licensed Property Manager
Southcorp Properties
09.2018 - 12.2021
Assistant Branch Manager
Southern Management Corporation
04.2017 - 09.2018
Licensed Pharmacy Technician
Rite Aid
03.2013 - 05.2016
Diploma
Blacksburg High School
Accredited Property Manager - Real Estate
South Carolina Real Estate Commission