Senior Controller – Short Term Rental Finance

About the role

Howard Financial is seeking a Senior Controller to own the financial reporting for its fast‑growing Short Term Rental (STR) vertical. You will be the primary financial steward for a portfolio of sophisticated clients, ensuring GAAP‑compliant, investor‑ready reporting while leading a remote accounting team.

Key responsibilities

• Portfolio Leadership: End‑to‑end financial reporting for STR clients, guaranteeing US GAAP compliance.
• Team Management: Lead, mentor and review a remote team of Senior Accountants, Accountants and Bookkeepers.
• Trust Accounting Oversight: Manage and reconcile complex owner‑fund and trust accounting structures.
• Month‑End Mastery: Drive a tight month‑end close, reconciling PMS data (Streamline, Guesty, Track) with general ledgers.
• Client‑Facing Communication: Act as strategic financial advisor, explaining P&L variances, cash‑flow projections and operational health.
• Process Scaling: Standardize workflows and implement internal controls as the vertical expands from 100 to 1,000+ properties.
• Audit & Compliance: 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 mastery of trust accounting and managing owner funds.
• Strong client‑facing professionalism, comfortable with CEOs and PE investors.
• System‑agnostic and tech‑savvy, able to work with various ERP platforms.

Required skills

• QuickBooks Online
• NetSuite
• Sage Intacct
• US GAAP
• Multi‑entity consolidations
• Trust accounting
• PMS systems (Streamline, Guesty, Track)