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 services, emphasizing accuracy, timeliness, and institutional-quality financial reporting.

Responsibilities

• Lead end-to-end financial reporting for a portfolio of Short Term Rental clients, ensuring compliance with US GAAP and delivering institutional-grade accuracy.
• Manage, mentor, and review a remote team comprising Senior Accountants, Accountants, and Bookkeepers.
• Oversee complex trust accounting structures, including management and reconciliation of "owner funds," ensuring 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 technical and strategic financial advisor to client leadership teams, explaining profit and loss 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 to 10+ years of experience in accounting or finance, 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.
• Mastery of trust accounting principles and fund management on behalf of property owners.
• Strong client-facing skills with the ability to communicate effectively with CEOs and private equity investors.
• Proficiency with accounting software such as QuickBooks Online, NetSuite, or Sage Intacct.
• Expert-level familiarity with PMS tools, specifically 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

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

Compensation & Benefits

• Opportunity to lead a high-complexity financial vertical serving sophisticated US investment platforms.
• Career growth potential with rapid scaling and a clear path to Director level based on performance.
• Ownership of a vertical with significant autonomy and responsibility.

Location

Remote position with a team distributed across various locations. Candidates must be comfortable working in a fast-paced startup environment and managing remote teams.