Senior Controller – Short Term Rental Vertical

About the role

Howard Financial is seeking a Senior Controller to lead its fast‑growing Short Term Rental vertical. You will own the financial reporting for a portfolio of vacation‑rental clients, ensure US GAAP compliance, and act as the primary financial advisor to CEOs and investors.

Key responsibilities

• Own end‑to‑end financial reporting for the Short Term Rental portfolio, guaranteeing institutional‑grade accuracy and US GAAP 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, resolving discrepancies between PMS data (Streamline, Guesty, Track) and general ledgers.
• Communicate financial insights to client leadership, explaining P&L variances, cash‑flow projections and operational health.
• Standardize workflows and implement internal controls as the vertical scales from 100 to 1,000+ properties.
• Coordinate external audits and ensure 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 leadership role.
• Deep experience in Short Term Rentals, Property Management or Hospitality.
• Comprehensive knowledge of US GAAP and multi‑entity consolidations.
• Expertise in trust accounting and managing funds on behalf of property owners.
• Proven ability to interact confidently with CEOs, private‑equity investors and other senior stakeholders.

Required skills

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