Senior Controller – Short Term Rental Vertical

About the role

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

Key responsibilities

• Own the full financial reporting cycle for the STR vertical, guaranteeing bullet‑proof balance sheets and US GAAP compliance.
• Lead, mentor and review a remote team of Senior Accountants, Accountants and Bookkeepers.
• Oversee complex “owner funds” and trust‑accounting structures, maintaining strict separation of client monies.
• Drive a tight month‑end close, reconciling PMS data (Streamline, Guesty, Track) with general ledgers and resolving discrepancies.
• Act as the strategic 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 portfolio expands from 100 to 1,000+ properties.
• Coordinate external audits and ensure all tax, sales‑tax and regulatory filings are supported by clean documentation.

Required profile

• 7–10+ years of accounting/finance experience, including at least 3 years in a Controller or senior finance 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 owner funds.
• Proven ability to communicate financial insights to CEOs, investors and private‑equity stakeholders.
• Comfortable working with a variety of finance systems and technology platforms.

Required skills

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