Senior Controller – Short Term Rental Finance

About the role

Howard Financial is seeking a Senior Controller to lead the financial operations of its fast‑growing Short Term Rental (STR) vertical. You will own end‑to‑end reporting for a portfolio of sophisticated vacation‑rental clients, ensuring US GAAP compliance and investor‑ready financial statements.

Key responsibilities

• Own the full financial reporting cycle for STR clients, delivering accurate balance sheets and P&L statements.
• Lead and mentor a remote team of Senior Accountants, Accountants, and Bookkeepers.
• Oversee complex trust accounting structures and reconcile owner‑funds with precision.
• Drive a tight month‑end close, resolving discrepancies between PMS data (e.g., Streamline, Guesty, Track) and general ledgers.
• Act as the primary financial advisor to client leadership, explaining variances, cash‑flow projections, and operational health.
• Standardize workflows, implement internal controls, and scale processes as the portfolio expands from 100 to 1,000+ properties.
• Coordinate external audits and ensure all tax, sales‑tax, and regulatory filings are fully documented.

Required profile

• 7–10+ years of accounting/finance experience, including at least 3 years in a Controller or senior leadership role.
• Deep expertise in Short Term Rentals, Property Management, or Hospitality.
• Comprehensive knowledge of US GAAP and multi‑entity consolidations.
• Proven experience managing trust accounting and owner‑fund structures.
• Strong client‑facing professionalism, comfortable presenting to CEOs and PE investors.

Required skills

• QuickBooks Online
• NetSuite
• Sage Intacct