Accounting Director (Vacation Rentals Industry)

COMPANY OVERVIEW: 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 90 professionals supports ~65 clients across a diverse range of industries. We recently reached $5M of contracted ARR and are growing rapidly (over 150% MRR growth YTD). POSITION SUMMARY: We're looking for an experienced Accounting Director who thrives on structure, precision, and getting things done right. In this role, you'll oversee trust accounting, owner statements, and multi-property financial operations across our vacation rental portfolio. You'll be the systems expert who ensures our PMS platforms, accounting software, and payment processors work seamlessly together—while leading a team that delivers accurate, timely financials and exceptional service to property owners. If you're detail-oriented, process-driven, and energized by building reliable systems in a fast-paced environment, this is your opportunity to make a major impact. RESPONSIBILITIES: 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 QUALIFICATIONS: 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) COMPENSATION & BENEFITS: Annual Salary: $150,000 Bonus Opportunity to earn bonus based on company's success and goals Benefits • Paid time off such as PTO, sick days, and vacation days Schedule Remote, 9-5 EST Remote About the Company: Better Talent Apply tot his job