Sr. Controller (Vacation Rental)

Senior Controller – Short-Term Rental & Hospitality

Location: Fully Remote

Employment Type: Full-time

About Howard Financial

Howard Financial provides outsourced financial solutions for fast-growing US companies. Founded in 2023, our team of ~100 professionals supports roughly 75 clients, driving over 200% year-over-year growth ($6M ARR). We operate with high autonomy, low red tape, and modern technology.

The Role

We are hiring a proactive, tech-forward Senior Controller to lead our rapidly growing Short-Term Rental (STR) & Hospitality vertical .

You will own the financial health of a portfolio of sophisticated clients, lead a remote team of accountants and bookkeepers, and serve as the main advisor for client executive teams. We need someone who loves solving complex financial puzzles, navigating trust accounting, and building scalable systems.

Deep STR experience is ideal, but we welcome strong Hospitality candidates who are tech-savvy fast learners.

What You’ll Do

• Portfolio Ownership: Lead end-to-end US GAAP financial reporting and month-end close for STR/Hospitality clients.
• Team Leadership: Mentor, guide, and review the work of a team of remote accountants and bookkeepers.
• Trust Accounting: Oversee complex owner-fund and trust accounting structures with absolute precision.
• Client Partnering: Act as the primary advisor for client CEOs and investors, explaining P&L trends and cash flow projections.
• Process Building: Implement scalable controls and standardize workflows as client portfolios expand.

What We’re Looking For

• Experience: 7+ years in accounting, with 3+ years in a Controller or senior financial leadership role.
• Domain Knowledge: Experience in Short-Term Rentals, Property Management, or Hospitality.
• Technical Accounting: Strong command of US GAAP, multi-entity consolidations, and trust accounting.
• Tech-Forward Mindset: Proficient in QBO, NetSuite, or Sage Intacct, plus PMS software (Guesty, Streamline, Track, or similar).
• Proactive Leader: A self-starter who digs into messy data, fixes inefficiencies, and communicates clearly with C-suite stakeholders.
• Language: Fluent spoken and written English.