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 ensure US GAAP‑compliant, investor‑ready statements for a portfolio of sophisticated clients while leading a remote accounting team.

Key responsibilities

• Lead end‑to‑end financial reporting for STR clients, guaranteeing accuracy and compliance.
• Manage and mentor a remote team of Senior Accountants, Accountants, and Bookkeepers.
• Oversee complex trust accounting, reconciling owner‑fund structures.
• Drive a tight month‑end close, resolving discrepancies between PMS data (Streamline, Guesty, Track) and general ledgers.
• Act as strategic financial advisor to CEOs and investors, 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 and regulatory filings.

Required profile

• 7–10+ years in accounting/finance, including 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 ability to manage trust accounting and client‑fund separation.
• Comfort presenting financial insights to senior leadership and investors.

Required skills

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

What we offer

• Opportunity to shape finance operations in a high‑growth startup.
• Leadership of a talented, remote accounting team.
• Exposure to venture‑backed clients and investors.