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Role Description

This role goes beyond traditional bookkeeping. You will own the financial operations, manage a complex accounting software ecosystem, and bring management-level oversight to the accounting function. As the primary financial point of contact for the executive team, you will utilize AI tools to drive efficiency, ensuring every entity is reconciled and every platform is operating correctly.

Key Responsibilities

• Financial Operations
  • Manage daily, weekly, and monthly bookkeeping across multiple entities, including deposits, reconciliations, vendor payments, and owner disbursements.
  • Perform month-end close and prepare clean financial reports for executive review.
  • Audit financial reports, owner statements, and platform data for total accuracy.
  • Coordinate with external CPAs for tax preparation and year-end reporting.
• Software & Systems Management
  • Administer and maintain Streamline PMS, Breezeway, Top Key, and QuickBooks Online as the primary systems manager.
  • Oversee data flow and integrations between platforms while identifying and resolving discrepancies.
  • Build and document financial SOPs to ensure software is configured correctly across all entities.
• AI & Automation
  • Leverage AI tools (ChatGPT, Claude, Gemini) and built-in software features to streamline reporting and data tasks.
  • Identify and implement automation opportunities to reduce manual work and improve data integrity.
• Communication & Collaboration
  • Deliver concise financial summaries to the executive team on a regular cadence.
  • Collaborate with operations and property care teams on expense tracking and job costing.
  • Utilize Slack, Microsoft Office 365, and OneDrive for team communication and documentation.

Qualifications

• 3+ years of bookkeeping or accounting experience managing multiple business entities.
• Hands-on proficiency with QuickBooks Online and experience with vacation rental or property management software (Streamline or similar PMS).
• Working knowledge of AI tools such as ChatGPT, Claude, or Gemini.
• Excellent written and verbal English communication skills with a self-directed work style.
• Experience building financial SOPs and workflow documentation is a plus.
• Background in the short-term rental, hospitality, or travel industry is highly preferred.
• QuickBooks ProAdvisor certification or familiarity with Breezeway and Top Key platforms.

Requirements

• Flexible schedule; US business hours availability required.
• Compensation: $1,800–$2,500/month + performance bonus.