Senior Controller – Short Term Rental Finance

About the role

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

Key responsibilities

• Lead the month‑end close process for a portfolio of STR properties, reconciling PMS data (Streamline, Guesty, Track) with general ledgers.
• Manage and reconcile complex owner‑funds and trust accounting structures, guaranteeing strict separation of client monies.
• Oversee a remote team of Senior Accountants, Accountants and Bookkeepers, providing mentorship and quality control.
• Act as the primary financial advisor to client leadership, explaining P&L variances, cash‑flow projections and operational health.
• Standardize workflows, implement internal controls and scale processes as the vertical expands from 100 to 1,000+ properties.
• Coordinate external audits and ensure accurate tax, sales‑tax and regulatory filings.

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 with trust accounting and managing owner funds.
• Strong client‑facing communication skills, comfortable presenting to CEOs and private‑equity investors.

Required skills

• QuickBooks Online
• NetSuite
• Sage Intacct
• Streamline (PMS)
• Guesty (PMS)
• Track (PMS)