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
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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
#J-18808-Ljbffr