Senior Controller – Short Term Rental Vertical

About the role

Howard Financial is seeking a Senior Controller to lead its rapidly expanding Short Term Rental (STR) vertical. You will own the financial reporting for a portfolio of sophisticated STR clients, ensuring US GAAP compliance and delivering investor‑ready reports.

Key responsibilities

• Own end‑to‑end financial reporting for the STR vertical, guaranteeing accuracy and compliance.
• Lead, mentor, and review a remote team of Senior Accountants, Accountants, and Bookkeepers.
• Manage and reconcile complex owner‑funds and trust accounting structures.
• Drive a tight month‑end close process, reconciling PMS data (Streamline, Guesty, Track) with general ledgers.
• Act as the strategic financial advisor for clients, explaining P&L variances, cash‑flow projections, and operational health.
• Standardize workflows, implement internal controls, and scale processes as the portfolio grows.
• Coordinate external audits and ensure clean documentation for 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.
• Extensive experience with trust accounting and managing funds on behalf of property owners.
• Strong client‑facing professionalism, comfortable presenting to CEOs and PE investors.
• Tech‑savvy and system‑agnostic, able to work with various accounting platforms.

Required skills

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