Senior Controller – Short Term Rental Vertical

About the role

Howard Financial is seeking a high‑caliber Senior Controller to own the financial reporting for its fast‑growing Short Term Rental (STR) vertical. You will ensure US GAAP‑compliant, investor‑ready reporting while leading a remote team of accountants and bookkeepers.

Key responsibilities

• Own end‑to‑end financial reporting for a portfolio of STR clients, guaranteeing US GAAP compliance.
• Lead, mentor and review the work of Senior Accountants, Accountants and Bookkeepers across a remote team.
• Manage and reconcile complex owner‑funds and trust accounting structures.
• Drive a tight month‑end close, reconciling PMS data (Streamline, Guesty, Track) with general ledgers.
• Act as strategic financial advisor to client leadership, explaining P&L variances and cash‑flow projections.
• Standardize workflows, implement internal controls and scale processes from 100 to 1,000+ properties.
• Coordinate external audits and ensure clean documentation for tax, sales‑tax and regulatory filings.

Required profile

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

Required skills

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