Sr. Controller (Vacation Rental Industry)

Overview

A rapidly growing financial services provider specializing in back-office solutions for high-growth companies is seeking a Senior Controller to lead its Short Term Rental (STR) vertical. The organization supports a diverse client base with bookkeeping, payroll, and customized reporting, emphasizing accuracy, timeliness, and institutional-quality financial management.

Responsibilities

• Lead end-to-end financial reporting for a portfolio of Short Term Rental clients, ensuring compliance with US GAAP and delivering investor-ready reports.
• Manage, mentor, and review a remote team comprising Senior Accountants, Accountants, and Bookkeepers, fostering accountability and precision.
• Oversee complex trust accounting structures, managing and reconciling "owner funds" to ensure impeccable separation of client funds.
• Drive a rigorous month-end close process, resolving discrepancies between Property Management System (PMS) data (e.g., Streamline, Guesty, Track) and General Ledgers.
• Serve as the primary financial advisor to clients, communicating P&L variances, cash flow projections, and operational health.
• Standardize workflows and implement internal controls to support scaling from 100 to over 1,000 properties.
• Coordinate external audits and ensure all tax, sales tax, and regulatory filings are supported by clean documentation.

Requirements

• 7–10+ years of accounting/finance experience, including at least 3 years in a Controller or senior leadership role.
• Deep industry expertise in Short Term Rentals, Property Management, or Hospitality.
• Comprehensive knowledge of US GAAP and multi-entity consolidations.
• Strong mastery of trust accounting and fund management on behalf of property owners.
• Professional client-facing skills, comfortable engaging with CEOs and private equity investors.
• Proficiency with accounting software such as QuickBooks Online, NetSuite, or Sage Intacct.
• Expert-level familiarity with PMS tools including Streamline, Guesty, Track, or Escapia.
• Ownership mentality with a proactive approach to problem-solving.
• Native-level or fully fluent English with exceptional written and verbal communication skills.

Preferred Qualifications

• Experience working in an accounting firm or business process outsourcing environment managing multi-client portfolios.
• Background with institutional or private equity-backed hospitality clients.
• Advanced data visualization skills using PowerBI, Tableau, or advanced Excel.

Compensation & Benefits

Details on compensation and benefits were not provided.

Location

Remote work environment with a distributed team supporting clients across various industries.