About Howard Financial

Howard Financial is a full-service back-office solution for companies and entities with bookkeeping, payroll, and bespoke reporting needs that require accuracy, timeliness, and institutional-quality reporting without the burden of full-time staff.

We are an experienced team of bookkeepers and administrators with multiple decades of combined experience across industries allowing companies to focus on their core business while we handle the rest.

Founded in 2023, our team of 60 professionals supports ~40 clients across a diverse range of industries. We recently reached $5M of contracted ARR and are growing rapidly (over 150% MRR growth YTD).

We are seeking a Director of Accounting with deep vacation rental industry experience to lead our accounting function across a growing, multi-property portfolio. This role is ideal for someone who knows that vacation rental accounting is not traditional hospitality accounting—and loves that challenge.

You’ll bring mastery of trust accounting, owner statements, PMS integrations, and the art of balancing accuracy with hospitality-grade service. Just as important, you’ll enjoy working with multiple owners, stakeholders, and internal teams, bringing clarity, confidence, and a bit of charm to complex financial conversations.

What You’ll Do

Vacation Rental & Trust Accounting Leadership

• Own and oversee trust accounting across multiple legal entities and property portfolios
• Ensure strict compliance with state trust laws, escrow requirements, and brand standards
• Maintain clean separation of operating funds, owner funds, and tax liabilities

Owner Statements & Client Relationships

• Oversee the preparation and accuracy of monthly owner statements
• Partner with Owner Relations and Operations to resolve owner inquiries with clarity and professionalism
• Translate complex financial data into owner-friendly explanations (you’re calm, confident, and kind—even during payout questions)

PMS & Systems Expertise

• Serve as the accounting lead for PMS platforms (e.g., Guesty, Escapia, Track, Streamline, Hostfully, or similar)
• Ensure seamless integration between PMS, accounting software (QuickBooks, Sage Intacct, NetSuite, etc.), and payment processors
• Troubleshoot reservation, folio, and payout discrepancies across systems

Multi-Property, Multi-Client Accounting

• Manage accounting operations across multiple properties, markets, and ownership structures
• Oversee revenue recognition for nightly rent, fees, taxes, commissions, and ancillary services
• Handle complex allocations, owner splits, management fees, and channel adjustments

Team Leadership & Process Improvement

• Lead, mentor, and develop an accounting team with a service-oriented mindset
• Establish scalable processes as the portfolio grows through onboarding, acquisitions, or new markets
• Drive month-end close, reconciliations, audits, and financial reporting

Compliance & Controls

• Oversee lodging tax compliance (state, county, city, special districts)
• Maintain internal controls and prepare for audits or owner reviews
• Partner with external CPAs, auditors, and banking partners

What We’re Looking For

Required Experience

• 7+ years of accounting experience, with direct vacation rental or short-term rental industry experience
• Proven trust accounting expertise in a property management or vacation rental environment
• Hands-on experience with owner statements and owner payout structures
• Strong working knowledge of PMS systems and their accounting workflows
• Experience supporting multi-property, multi-entity portfolios
• Advanced knowledge of accounting platforms (QuickBooks, Sage Intacct, NetSuite, or similar)

Preferred

• CPA or equivalent professional certification
• Experience with portfolio growth, acquisitions, or market expansion
• Familiarity with channel managers, payment processors, and tax automation tools