Executive Assistant & Short-Term Rental Operations Virtual Assistant

Full-Time Executive Assistant & Short-Term Rental Operations Virtual Assistant

Job Description

Client Industry: Real Estate / Short-Term Rental / Property Management

Employment Type: Full-Time

Work Setup: Remote

Client Location: Canada

Salary: PHP 50,000

Role Summary

We are seeking a highly organized, proactive, and resourceful Executive Assistant & Short-Term Rental Operations Virtual Assistant to support a growing real estate portfolio that includes short-term rentals, long-term rentals, new construction, and property renovation projects.

This role combines executive support, property operations, guest communication, real estate administration, and systems management. The ideal candidate will help centralize day-to-day operations, keep multiple properties and projects organized, and build systems that allow the business owner to focus on acquisitions, renovations, and business growth.

This is a long-term opportunity for someone who enjoys working across different areas of a growing business, solving operational problems, and creating structure where processes are still developing.

Project summary

We will recruit and place a full-time Executive Assistant & Short-Term Rental Operations Virtual Assistant to support Andrienne across her growing real estate portfolio, including short-term rentals, long-term rentals, new construction, and property renovations. The primary objective is to eliminate administrative bottlenecks, implement scalable systems, and free Andrienne to focus on acquisitions, renovations, and business growth.

Short-Term Rental Operations

• Manage guest communications across Airbnb, VRBO, and OwnerRez
• Coordinate reservations, guest inquiries, reviews, and issue resolution
• Coordinate with cleaners, maintenance vendors, and contractors
• Monitor property operations and daily administrative tasks
• Support revenue management and listing updates

Administrative & Executive Support

• Manage email, calendar, and daily communications
• Organize paperwork and digital files
• Track follow-ups, projects, and action items
• Prepare documents and provide general administrative support
• Assist with scheduling across multiple businesses

Real Estate Operations

• Support long-term rental administration
• Assist with tenant screening and documentation
• Coordinate contractor communications and renovation projects
• Research investment properties and support acquisition activities
• Maintain organized records across multiple properties

Systems & Technology

• Implement and maintain SOPs using Notion or similar platforms
• Organize business systems, passwords, and documentation
• Support CRM implementation and workflow automation
• Help optimize the technology stack to improve operational efficiency
• Continuously document repeatable processes as the business grows

Key Responsibilities

Short-Term Rental Operations

• Manage guest communications across Airbnb, VRBO, OwnerRez, and related platforms.
• Respond to guest inquiries and reservation-related requests.
• Coordinate check-ins, check-outs, and other guest-related activities.
• Monitor and respond to guest reviews.
• Assist with resolving routine guest issues and escalating complex issues when necessary.
• Coordinate cleaners, maintenance vendors, contractors, and other service providers.
• Monitor property readiness and day-to-day operational requirements.
• Update property and listing information as needed.
• Support revenue management activities and maintain accurate reservation information.

Executive & Administrative Support

• Manage and organize email communications.
• Maintain calendars, appointments, and scheduling across multiple businesses.
• Track priorities, follow-ups, projects, and action items.
• Prepare documents, reports, and correspondence.
• Organize digital files, paperwork, and business records.
• Assist with day-to-day administrative responsibilities.
• Proactively follow up on outstanding tasks and ensure deadlines are not missed.

Real Estate & Property Operations

• Support administration of long-term rental properties.
• Assist with tenant screening and related documentation.
• Maintain organized tenant and property records.
• Coordinate communications with contractors and service providers.
• Support renovation and new construction projects.
• Track project activities, timelines, and outstanding tasks.
• Research potential investment properties and assist with acquisition-related research.
• Maintain accurate records across multiple properties and projects.

Systems & Technology

• Implement and maintain SOPs using Notion or similar platforms.
• Document repeatable business and property management processes.
• Organize operational documentation and business systems.
• Assist with organizing password and access management systems.
• Support CRM implementation and workflow automation.
• Help optimize the business technology stack.
• Identify opportunities to improve efficiency through better systems and processes.

Standards

Core Requirements

• Previous experience as an Executive Assistant, Operations Assistant, Property Management Assistant, Real Estate Virtual Assistant, or similar role.
• Strong written and spoken English communication skills.
• Excellent organizational and time management abilities.
• Strong attention to detail.
• Ability to manage multiple properties, projects, and priorities simultaneously.
• Strong problem-solving and critical thinking skills.
• Comfortable working independently in a remote environment.
• Proactive approach to identifying and resolving operational issues.
• Ability to handle confidential business, tenant, and guest information professionally.
• Reliable internet connection and suitable remote work setup.

Technical Skills (Required or Strong Advantage)

Required

• Google Workspace
• Microsoft Office
• Google Sheets / Excel
• Email and calendar management
• Cloud file storage and document organization
• Basic internet research

Strong Advantage

• Airbnb
• VRBO
• OwnerRez
• Notion
• Property management systems
• CRM platforms
• Workflow automation tools
• Project management platforms such as ClickUp, Asana, Trello, or Monday.com
• DocuSign or electronic signature platforms
• Password management tools
• AI productivity tools such as ChatGPT

Nice-to-Have

• Previous experience in short-term rental operations.
• Experience with OwnerRez or another property management system.
• Real estate or property management experience.
• Experience supporting multiple rental properties.
• Experience coordinating cleaners, contractors, and maintenance vendors.
• Experience with renovation or construction project coordination.
• Experience with tenant screening and long-term rental administration.
• Experience researching real estate investment opportunities.
• SOP creation and process documentation experience.
• Experience implementing business systems or automations.
• Basic understanding of revenue management for short-term rentals.

Work Ethic & Behavioral Expectations

• Highly organized and dependable.
• Proactive rather than waiting for instructions for every task.
• Comfortable managing multiple priorities and switching between different types of work.
• Detail-oriented and committed to maintaining accurate records.
• Resourceful and confident solving routine operational problems.
• Professional and personable when communicating with guests, tenants, vendors, and business contacts.
• Comfortable working independently while knowing when to escalate an issue.
• Process-oriented and interested in building systems that make the business easier to operate.
• Adaptable to changing priorities as the real estate portfolio grows.
• Accountable for following tasks through to completion.
• Interested in continuously improving workflows, documentation, and operational efficiency.

Success Metrics

First 30 Days

• Become familiar with the property portfolio, business priorities, and existing systems.
• Learn the client's short-term rental platforms and operational workflows.
• Successfully manage routine guest communications and administrative tasks.
• Establish organized systems for tracking priorities, property issues, and follow-ups.
• Build familiarity with vendors, contractors, and recurring property operations.

Within 90 Days

• Independently manage routine short-term rental operations with minimal supervision.
• Maintain timely and professional guest communications.
• Coordinate cleaners, maintenance requests, and vendors effectively.
• Keep property, tenant, and project records accurate and organized.
• Begin documenting and improving recurring workflows through SOPs and business systems.
• Provide reliable administrative and executive support across the portfolio.

Ongoing Success

• Keep short-term rental operations running smoothly and proactively.
• Reduce administrative bottlenecks and prevent important tasks from falling through the cracks.
• Maintain accurate and organized property, tenant, vendor, and project records.
• Continuously improve SOPs, technology, and operational workflows.
• Provide the business owner with greater visibility and control across the portfolio.
• Take increasing ownership of property operations and administrative responsibilities as the portfolio grows.
• Help create scalable systems that allow the real estate business to expand without creating a proportional increase in administrative workload.