Executive Assistant/Bookkeeping & Property Management Support

The successful candidate will function as an

Executive Assistant, Office Manager, Bookkeeping Support Specialist, and

Property Management Coordinator while gradually taking ownership of

recurring operational workflows.

Key Responsibilities

1. Executive Assistant & Office Support

● Support daily office operations and administrative functions.

● Manage email inboxes, organize correspondence, identify priorities, and draft responses as directed.

● Coordinate calendars, schedule meetings, appointments, reminders, and recurring tasks.

● Keep digital documents, files, and business information organized and accessible.

● Assist with both business and personal administrative tasks as needed.

●

Serve as a trusted right-hand partner, helping manage priorities,

reduce overwhelm, and ensure deadlines and commitments are met.

● Learn and follow the client's preferred systems, processes, and communication style.

● Take ownership of recurring administrative responsibilities as training and trust develop.

● Function as an Office Manager–type resource, supporting administrative operations and workflow coordination.

● Proactively anticipate needs by preparing meeting links, documents, reminders, and follow-up actions.

●

Recommend and implement workflow improvements, systems, and operational

efficiencies that increase productivity and reduce manual work.

● Help create structure, organization, and accountability across daily activities and business operations.

2. Bookkeeping & Financial Administration Support

● Provide bookkeeping support using QuickBooks Online.

● Categorize receipts, expenses, and transactions accurately.

● Organize and file receipts using NEAT.

● Track business and property-related expenses.

● Maintain clean, accurate, and confidential financial records.

● Identify and escalate missing receipts, unclear transactions, or items requiring client review.

● Assist with financial organization, documentation, and basic reporting support.

● Support invoice tracking and bill management as needed.

● Help streamline bookkeeping and financial administration processes.

3. Short-Term Rental & Property Management Support

● Provide administrative support for short-term rental properties.

● Monitor, organize, and respond to guest messages through Airbnb, Vrbo, Hostaway, and similar platforms when authorized.

● Coordinate cleaning schedules and follow up with cleaners, vendors, maintenance providers, and contractors.

● Track maintenance items, property-related tasks, and operational follow-ups.

● Organize documentation related to insurance claims, property issues, and vendor communication.

● Escalate guest, vendor, or property concerns when client approval is required.

● Help maintain high hospitality and service standards across all rental properties.

● Gradually take ownership of recurring rental operations and workflows as training progresses.

● Support the continued growth and smooth day-to-day management of the client’s short-term rental portfolio.

4. Email, Calendar & Communication Support

● Manage and organize email communication, identifying urgent items and prioritizing responses.

● Draft professional responses and maintain clear, timely communication with the client.

● Coordinate follow-up actions to ensure tasks, messages, and requests are completed.

● Communicate professionally with vendors, service providers, guests, and business contacts.

● Support scheduling, meeting preparation, reminders, and follow-up as needed.

● Proactively prepare meeting links, materials, and relevant information for upcoming meetings.

5. Software, Technology & Systems Support

The ideal candidate should be familiar with or able to quickly learn:

● Microsoft Office

● QuickBooks Online

● NEAT

● MLS

● Airbnb

● Vrbo

● Hostaway or similar property management platforms

● Loom

● Zoom

● Slack or similar communication platforms

● Email and calendar systems

● Digital filing and document management tools

● AI productivity tools and automation platforms

6. Problem Solving & Process Improvement

● Identify ways to simplify workflows and improve operational efficiency.

● Suggest improvements to bookkeeping, office, email, and property management processes.

● Troubleshoot issues, research solutions, and ask thoughtful questions before escalating.

● Create repeatable systems that support automation, delegation, and better organization.

● Respectfully challenge inefficient processes when appropriate.

● Take initiative in solving problems, reducing administrative burden, and supporting business growth.

Requirements

Required Skills & Experience

●

2–3+ years of experience supporting executives, business owners,

entrepreneurs, real estate professionals, or professional service

leaders.

● Bachelor’s degree in Business Administration,

Commerce, Communications, Finance,Accounting, Real Estate, Project

Management, or a related field preferred.

● Experience as

an Executive Assistant, Administrative Assistant, Office

Manager,Operations Assistant, Bookkeeping Assistant, or similar role.

●

Basic bookkeeping experience, including familiarity with QuickBooks

Online, receipt organization, expense categorization, and financial

record keeping.

● Strong Microsoft Office skills and general technology aptitude, with the ability to learn

new software quickly.

● Excellent written and spoken English communication skills with a clear,professional tone.

● Highly organized and detail-oriented, with strong follow-through and the ability to

manage multiple priorities.

● Able to work independently after training, take initiative, and solve problems proactively.

● Comfortable supporting both business and personal administrative responsibilities.

● Professional, dependable, trustworthy, discreet, and service-oriented.

● Able to anticipate needs, manage upward, and help keep the client organized, focused,and accountable.

● Confident recommending solutions, process improvements, and better tools when appropriate.

● Comfortable crea