Inside Out Hiring

About the Client: 

The client is a full-service short-term rental company dedicated to helping real estate investors significantly increase their monthly cash flow from their properties. The company operates as a complete, "done for you" solution, either by partnering with owners to share in revenue or by directly leasing vacant units for use as premium short-term accommodations. For property owners, this hands-off arrangement allows them to earn higher than traditional market rents, receive automatic monthly payments, and avoid any fees or hidden costs. The business manages all operational aspects, which includes ensuring professional daily and weekly cleanings, providing secure keyless entry, and covering minor maintenance. Their guests are carefully selected business and leisure travelers seeking an "un-hotel" experience, which results in minimal wear and tear on the properties compared to traditional tenants.

About the Role:
 

The client seeks a resourceful and highly organized Executive Assistant to be the backbone of his short-term rental management business. You'll handle essential property operations, including coordinating with vendors and cleaners, managing bill payments, and organizing critical financial documents. The role requires strong administrative skills like inbox and calendar management, coupled with a proactive approach to utilizing AI tools for efficiency. Initially part-time (20 hours/week), this position is designed to quickly grow into a full-time management role as the business scales its property portfolio. This is a crucial opportunity for a long-term partner ready to streamline operations and contribute to business expansion.

Key Responsibilities

Property Operations and Coordination

• Vendor Management: Handle all communications and coordination with cleaners, handymen, and other vendors for maintenance and regular services across all properties.
• Financial Coordination: Coordinate payments for bills, manage expenses, and perform basic organizational bookkeeping, including categorizing business transactions and tracking receipts.
• Document Management: Organize and categorize important business documents, including legal correspondence and vendor contracts.
• Guest Communication (Secondary): Ideally, assist with general guest communications as comfort and skill level increase.

Executive and Administrative Support

• Inbox Management: Manage and organize the principal's email inbox, categorizing messages and responding where appropriate or as directed.
• Calendar Management: Proactively manage and schedule the principal's business calendar.
• Workflow Organization: Maintain organized systems and workflows to ensure smooth daily operations.

Personal Administration

• Appointment Scheduling: Schedule and coordinate personal appointments.
• Personal Coordination: Coordinate schedules and communications involving the principal's wife and children.
• Grocery/Item Ordering: Handle personal tasks such as grocery or item ordering.

Qualifications & Skills

• Strong Organizational Skills: Proven ability to manage and categorize multiple tasks, emails, and documents for multiple properties/projects simultaneously.
• Proactivity: Must be self-driven, efficient, and able to identify and tackle tasks without constant direction.
• Excellent Communication: Strong written and verbal English communication skills for professional interaction with vendors, partners, and internal teams.
• Technology & AI Familiarity: Comfortable and proficient in utilizing AI tools (e.g., ChatGPT) to enhance efficiency and streamline various tasks without needing step-by-step instruction.
• Basic Bookkeeping: Experience or aptitude for categorizing transactions and organizing financial documentation. Quickbooks and Google Sheets/Excel experience would be beneficial.
• Growth Mindset: An individual who desires a long-term role with the potential to grow into a more senior Operations Manager role as the business expands.
• Commitment: Dedicate to this job and won't be working on outside jobs during working hours.
• (Nice-to-Have) Social Media/Content Experience: Experience in social media or content creation would be a significant advantage, potentially allowing the VA to take on a broader, full-time role sooner by managing brand presence and content strategy.