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).

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.

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 (Quick Books, Sage Intacct, Net Suite, 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

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 (Quick Books, Sage Intacct, Net Suite, or similar)

$150,000

Opportunity to earn bonus based on company's success and goals

• Paid time off such as PTO, sick days, and vacation days

Remote, 9-5 EST