Property Manager & Executive Assistant

I am looking for a highly organized, proactive, and dependable Property Manager & Executive Assistant to support the day-to-day operations of my real estate and short-term rental business. This is a hands-on role for someone who can manage details, communicate professionally, follow systems, solve problems independently, and keep me ahead of deadlines. The ideal candidate is not someone who simply waits for instructions—you should be able to identify what needs to be done and take ownership of it. You will support both property management operations and executive/administrative responsibilities, helping ensure properties, tenants, guests, vendors, and business operations run smoothly. Key Responsibilities Property Management Manage day-to-day operations for short-term and long-term rental properties Monitor Airbnb/Hostaway and other property management platforms Respond to guest and tenant questions professionally and promptly Coordinate maintenance requests and follow up with vendors Coordinate cleaners, inspections, repairs, and property turnovers Monitor property readiness before guest check-ins Track maintenance issues, repairs, supplies, and outstanding tasks Communicate with contractors, cleaners, tenants, and guests Maintain accurate property records and documentation Help identify operational issues before they become larger problems Assist with guest complaints, refunds, and issue resolution Ensure property standards, house rules, and operating procedures are followed Track invoices, payments, vendor information, and other property-related documentation Executive Assistant Responsibilities Manage my task list and help prioritize daily/weekly responsibilities Organize appointments, meetings, and follow-ups Maintain calendars and important deadlines Prepare meeting agendas, notes, and action items Follow up with team members and vendors to ensure tasks are completed Draft professional emails, messages, notices, and communications Organize files, documents, spreadsheets, and business information Research vendors, services, products, and business-related information Help create and maintain SOPs and operational systems Provide regular updates on outstanding tasks and priorities Keep me informed of anything requiring my attention or decision Technology & Systems You should be comfortable learning and working across multiple platforms, including: Airbnb Hostaway TenantCloud Google Workspace Google Drive Google Calendar Google Sheets QuickBooks Monarch Money Slack or similar communication platforms Canva Zoom Upwork Experience with property-management software is strongly preferred. What I'm Looking For The right person is: Extremely organized Detail-oriented without losing sight of the big picture A strong written and verbal communicator Proactive and able to work independently Comfortable managing multiple priorities Excellent at follow-up Good at problem-solving Reliable and accountable Comfortable working with deadlines Professional when communicating with tenants, guests, vendors, and team members Tech-savvy and able to learn new software quickly Comfortable taking ownership rather than constantly asking what to do next You must be able to: See a problem → determine the next step → take action → follow up → communicate the result. That mindset is extremely important for this role. Hours & Availability This position will begin as a part-time role, with the potential to increase hours and responsibilities based on performance and business needs. Some flexibility may be required for urgent property-management issues, guest/tenant communications, or time-sensitive vendor matters. Compensation Compensation will be based on experience, skill level, availability, and overall fit. Please include your hourly rate and your preferred weekly availability in your proposal. How to Apply Please answer the following questions in your proposal: Tell me about your experience as a Property Manager, Executive Assistant, or both. How many properties have you managed or supported? Which property-management platforms have you used? What systems have you used to manage tasks, follow-ups, and deadlines? Describe a time you identified a problem without being asked and took the initiative to solve it. How do you prioritize when several urgent tasks come up at the same time? What is your hourly rate? What days and hours are you available? Important: I am looking for someone who wants to become a trusted long-term member of the business—not someone who simply completes isolated tasks. Reliability, initiative, communication, and ownership are extremely important to me.