Associate Director

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 Associate Director to help lead the accounting function for our Vacation Rental portfolio. Reporting to the Accounting Director, you'll own financial reporting for a group of client engagements, lead and develop a team of senior accountants and accountants, and serve as a trusted point of contact for client leadership. This role suits someone who is ready to step into broader leadership, has worked in fast-paced, investor-backed environments, and enjoys building scalable processes as much as delivering results.

What You'll Do

• Manage month-end and year-end close for an assigned portfolio of vacation rental clients, reviewing work and ensuring accurate, timely financial statements.
• Lead, mentor, and develop a team of senior accountants and accountants, providing day-to-day guidance and quality review.
• Serve as the primary point of contact for client finance and operations leaders, presenting monthly results and translating numbers into operational insights.
• Oversee trust accounting, owner statements, and reconciliations specific to vacation rental and property management operations.
• Prepare and review investor and management reporting packages, including VR-specific KPIs such as RevPAR, occupancy, ADR, and owner payouts.
• Identify and implement improvements to close processes, internal controls, and accounting policies, in partnership with the Accounting Director.
• Support audits, tax coordination, due diligence, and integration work as clients grow through acquisition.
• Collaborate with Howard's FP&A and advisory teams on budgeting, forecasting, and cash management.
• Champion the adoption of technology and automation across the accounting stack.

What We're Looking For

• 6+ years of progressive accounting experience, including 2+ years leading or reviewing the work of others (Senior Accountant, Controller, or Accounting Manager).
• 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.
• Clear, confident communication with client executives, owners, and internal leadership.
• Hands-on experience with accounting systems such as QuickBooks Online, Xero, NetSuite, or Sage Intacct, plus PMS integrations like Guesty, Track, Streamline, or Escapia.
• CPA or equivalent certification preferred, or actively pursuing.

Highly Preferred

• Experience at a private equity–backed company, including investor reporting, lender covenants, or roll-up integrations.
• Background in an outsourced accounting, fractional CFO, or advisory firm, 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.
• A clear growth path toward Director-level leadership in a growing, tech-forward firm.