Remote Accounting Director for Vacation Rentals

About Howard Financial
Howard Financial is a tech-forward outsourced accounting and finance firm that partners with growing companies across Vacation Rental, Hospitality, Consumer & E-Commerce, and Development & Real Estate. We combine deep industry expertise with modern tools to give our clients the financial clarity they need to scale.

The Role
We're looking for an Accounting Director to lead the accounting function for our Vacation Rental portfolio. You'll own the integrity of financial reporting across multiple client engagements, lead and develop a team of controllers and accountants, and act as a trusted advisor to client leadership, including founders, operators, and investors. This role suits someone who has worked in fast-paced, investor-backed environments and who enjoys building scalable processes as much as delivering results.

What You'll Do

• Oversee month-end and year-end close across a portfolio of vacation rental clients, ensuring accurate and timely financial statements.
• Lead, mentor, and scale a team of controllers, senior accountants, and accountants.
• Serve as the senior point of contact for client executives, presenting financial results and translating numbers into operational insights.
• Own trust accounting, owner statements, and reconciliations specific to vacation rental and property management operations.
• Prepare investor and board-level reporting packages, including KPI dashboards tailored to the VR industry, such as RevPAR, occupancy, ADR, and owner payouts.
• Design and improve accounting policies, internal controls, and close processes that scale with client growth.
• Support audits, tax coordination, due diligence, and M&A or integration activity as clients grow through acquisition.
• Partner with Howard's FP&A and advisory teams on budgeting, forecasting, and cash management.
• Drive adoption of technology and automation across the accounting stack.

What We're Looking For

• 8+ years of progressive accounting experience, including 3+ years in a leadership role (Controller, Senior Controller, or Accounting Director).
• Strong command of US GAAP and accrual accounting.
• Experience in vacation rental, property management or hospitality accounting.
• Proven ability to manage multiple entities or client engagements at once.
• Excellent communication skills, with confidence presenting to executives, owners, and investors.
• Hands-on experience with accounting systems such as Quick Books Online, Xero, Net Suite, or Sage Intacct, plus PMS integrations like Guesty, Track, Streamline, or Escapia.
• CPA or equivalent certification preferred.

Highly Preferred

• Experience at a private equity–backed company, including investor reporting, lender covenants, roll-up integrations, or exit preparation.
• Background in a fractional CFO or outsourced finance firm, with experience managing several client relationships at the same time.

Why Howard

• Competitive compensation, aligned with experience.
• Fully remote, flexible work environment.
• Exposure to diverse, high-growth companies in a niche industry.
• The opportunity to shape the accounting function of a growing, tech-forward firm.