Executive Assistant & Bookkeeper

Bookkeeping & Reporting Scope
• Transaction entry and categorization across multiple entities (QuickBooks Online).
• Monthly reconciliations (bank, credit card, loans) and aging reviews (A/P & A/R).
• Monthly financial report preparation (P&L, Balance Sheet, Cash Flow).
• Vendor electronic payments, invoicing, and receipt management.
• Coordinate as needed with CPA or leadership for month-end close and filings.
• Intercompany transfer tracking: Not applicable (N/A).
Short-Term Rental (STR) Management Scope
• Manage 10 properties in Guesty: guest communications, inquiry responses, and reviews.
• Coordinate cleanings/turnovers and vendor scheduling; ensure quality standards.
• Maintain listing calendars, availability, and pricing rules within platform settings.
• Monitor occupancy, ADR, and revenue reports; flag issues and recommend optimizations.
• Ensure timely resolution of maintenance issues and maintain vendor records.
Tools & Technology
• Accounting: QuickBooks Online (required).
• Short-Term Rentals: Guesty (experience desired, not required).
• Productivity: Microsoft 365 and Google Workspace (both required).
• File Storage: OneDrive/SharePoint and Google Drive (both required).
• Social: LinkedIn, Facebook, Instagram (basic scheduling and engagement).
• Other: Familiarity with standard office apps (Word, Excel, PowerPoint, Docs, Sheets).
Required Qualifications
• Minimum 2 years’ experience in an executive assistant and/or bookkeeping role.
• QuickBooks Online proficiency (transaction entry, reconciliations, reports).
• Proficiency in Microsoft 365 and Google Workspace (email, calendar, docs, sheets).
• Excellent written and verbal English; timely, professional communication.
• High attention to detail, discretion with confidential information, and reliability.
• Ability to work across multiple entities, priorities, and inboxes concurrently.
• Available during Eastern Time business hours; comfortable as an independent contractor.
Preferred Qualifications
• Experience with Guesty or comparable STR management platforms.
• Familiarity with EOS tools and rhythms (L10s, Scorecard, Rocks, V/TO).
• Basic social media scheduling and content coordination (LinkedIn, Facebook, Instagram).
• Experience working with international/remote teams and multi-entity operations.
Core Values & Success Traits
• Golden Rule: Treat clients, guests, vendors, and teammates with respect and integrity.
• Work Is Our Calling: Take ownership, pursue excellence, and follow through.
• GWC (Gets it, Wants it, Capacity to do it): Demonstrate competence, desire, and bandwidth.
• Proactive, resourceful, and detail-oriented; anticipates needs and solves problems.
• Trustworthy, confidential, and responsive; protects sensitive information.
Hours, Work Arrangement & Compensation
• Status: Independent Contractor.
• Schedule: Part-time (25 hours/week) with a planned transition to full-time within 6 months.
• Work Location: Remote (international candidates welcome); must work Eastern Time business hours.
• Compensation: Commensurate with experience.