Executive Assistant / Property Management Associate

Executive Assistant / Property Management Associate

Location: Remote flexibility
Compensation: 1,500 - 1,700USD
Industry: Hospitality & Property Management
Schedule: Set hours adhering to Pacific Standard Time (Mid-May to Mid-October), with flexible hours including evenings. Potential for supplemental work during off-season.

About the Role
We are seeking a versatile and proactive Executive Assistant / Property Management Associate to support a busy, seasonal motel operation. This hybrid role combines guest and tenant communications, property management tasks, and internal administrative support. The ideal candidate will be highly organized, tech-savvy, and skilled at managing communications with warmth and professionalism.

This position is pivotal to ensuring smooth day-to-day operations during the busy season, with the potential to evolve into a year-round role depending on business needs. You’ll be at the heart of our operations—managing schedules, streamlining communications, and supporting guest experiences across platforms.

In addition, you will work directly with the owner of the company. This will largely be in helping scheduling, participating in meetings, following up with duties to be completed after the meetings, and will help him maintain organization.

What You’ll Do

Property Management & Guest Communications

• Manage inbound and outbound communications with guests and tenants using Whistle (text messaging platform)
   
• Oversee bookings and reservations via Cloudbeds; troubleshoot or escalate guest concerns as needed
   
• Support seasonal leasing processes for tenants and respond to prospective tenant inquiries
   
• Maintain an active presence on communication channels to ensure prompt, professional engagement
   

Administrative & EA Support

• Provide executive assistance including scheduling, internal communications, and coordination with vendors or partners
   
• Maintain light bookkeeping and records management, ensuring timely documentation and updates
   
• Assist with the coordination of property maintenance and vendor scheduling
   
• Organize internal systems and workflows to improve team efficiency
• Provide organization methods of sales contracts, buyer communication, scheduling
• Assist with updating websites
   

Tech Stack You’ll Work With

• Whistle (Guest communication system)
   
• Cloudbeds (Hospitality booking and reservation platform)
   
• Yardi Breeze Premiere (Property management platform – experience preferred but training available)
• Familiar with QUICKBOOKS
   
• Familiarity with alternatives like AppFolio or similar platforms is a plus
• MS Excel

What We’re Looking For

• 2–5 years of experience in hospitality operations, property management, or executive assistance
   
• Strong written and verbal communication skills with a customer-first approach
   
• Comfortable managing high-volume communications and balancing multiple systems
   
• Tech-savvy with an ability to quickly learn and navigate cloud-based platforms
   
• Highly organized, detail-oriented, and dependable - especially during the high season
   
• Ability to work independently with a proactive mindset
   
• Flexible availability, including evenings and weekends during peak season
   

Nice to Have

• Experience using Yardi Breeze Premiere or comparable systems like AppFolio
   
• Familiarity with seasonal property or hospitality operations
   
• Bilingual (if Spanish) or multilingual communication skills
   

Why Join Us?

• Opportunity to take ownership of a critical hybrid role in a dynamic seasonal business
   
• Flexibility to work remotely with the option to remain involved year-round
   
• Chance to grow within a collaborative and innovative team
   
• Training provided for the right candidate - bring your adaptability and eagerness to learn!