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 vacation‑rental clients, ensuring GAAP‑compliant, investor‑ready statements while leading a remote accounting team.

Key responsibilities

• Oversee end‑to‑end financial reporting for STR clients, guaranteeing US GAAP compliance and institutional‑grade accuracy.
• Lead, mentor and review the work of Senior Accountants, Accountants and Bookkeepers across multiple time zones.
• Manage complex trust‑accounting structures, reconciling owner funds and ensuring strict segregation of client monies.
• Drive a tight month‑end close, resolving discrepancies between property‑management system data (e.g., Streamline, Guesty, Track) and general ledgers.
• Act as a 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 leadership role.
• Deep expertise in Short Term Rentals, property management or hospitality.
• Comprehensive knowledge of US GAAP and multi‑entity consolidations.
• Proven experience with trust accounting and managing owner funds.
• Strong client‑facing communication skills, comfortable presenting to CEOs and private‑equity investors.

Required skills

• QuickBooks Online
• NetSuite
• Sage Intacct
• Property‑management systems such as Streamline, Guesty, Track