Executive Assistant, Property Management & Short-Term Rental Operations

This is a fully remote position, open to applicants in Canada.

📋 Description

• Oversee guest interactions on platforms such as Airbnb, VRBO, OwnerRez, and others.

• Address guest questions and handle reservation-related inquiries.

• Manage check-ins and check-outs, reviews, issue resolution, and coordinate with cleaners, maintenance vendors, contractors, and service providers.

• Supervise property readiness and daily operational needs.

• Update property information and listings accordingly.

• Assist with revenue management tasks and ensure accurate reservation data.

• Organize and manage email correspondence, calendars, appointments, and scheduling across various businesses.

• Monitor priorities, follow-ups, projects, action items, and deadlines.

• Prepare documents, reports, and correspondence while providing general administrative support.

• Systematize digital files, paperwork, business records, passwords, and access documentation.

• Aid in long-term rental management, tenant screening, and related documentation.

• Facilitate communications with contractors and support renovation and new construction initiatives.

• Track project activities, timelines, and pending tasks.

• Conduct research on potential investment properties and assist with acquisition-related inquiries.

• Implement and uphold standard operating procedures (SOPs) using Notion or similar platforms.

• Document repeatable processes in business and property management.

• Support the implementation of CRM systems and workflow automation.

• Enhance the business technology stack and pinpoint areas for improved efficiency.

• Create organized systems for tracking priorities, property issues, and follow-ups.

• Assume greater responsibility for property operations and administrative tasks as the portfolio expands.

⛳️ Requirements

• Prior experience in roles such as Executive Assistant, Operations Assistant, Property Management Assistant, Real Estate Virtual Assistant, or similar positions.

• Proficient written and verbal communication skills in English.

• Exceptional organizational and time management skills.

• Keen attention to detail.

• Capability to manage multiple properties, projects, and priorities at once.

• Strong problem-solving abilities and critical thinking skills.

• Comfortable working autonomously in a remote setting.

• Proactive in identifying and resolving operational challenges.

• Ability to handle confidential business, tenant, and guest information with professionalism.

• Reliable internet connection and a suitable setup for remote work.

• Required: Proficiency in Google Workspace.

• Required: Proficiency in Microsoft Office.

• Required: Knowledge of Google Sheets / Excel.

• Required: Experience with email and calendar management.

• Required: Familiarity with cloud file storage and document organization.

• Required: Basic internet research skills.

• Strong advantage: Experience with Airbnb, VRBO, OwnerRez, Notion, property management systems, CRM platforms, workflow automation tools, project management platforms, DocuSign or electronic signature platforms, password management tools, and AI productivity tools like ChatGPT.

• Previous experience in short-term rental operations, real estate, or property management is desirable.

• Experience managing multiple rental properties is beneficial.

• Familiarity with coordinating cleaners, contractors, and maintenance vendors is a plus.

• Experience in renovation or construction project management is advantageous.

• Experience in tenant screening and long-term rental management is a plus.

• Experience in researching real estate investment opportunities is a plus.

• Experience in SOP creation, process documentation, business systems, and automation is a nice-to-have.

• Basic understanding of revenue management for short-term rentals is a nice-to-have.

• Highly organized, reliable, proactive, adaptable, resourceful, and process-oriented.

• Eager to continuously improve workflows, documentation, and operational efficiency.

🏝️ Benefits

• Full-time remote work arrangement.

• Long-term career opportunity.

• Chance to work across short-term rentals, long-term rentals, new construction, and renovation projects.

• Opportunity to develop scalable systems and enhance operational efficiency.