Controller US Vacation Rentals

Howard Financial is a full-service back-office solution for high-growth companies 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 ~100 professionals supports ~75 clients across a diverse range of industries. We recently reached $6M of contracted ARR and are growing rapidly (over 200% LTM growth).

As a Controller at Howard, you will be responsible for the financial integrity of a portfolio of Vacation Rental clients. You will bridge the gap between day-to-day bookkeeping and executive-level financial strategy. This role requires a professional who deeply understands the unique accounting challenges of the Short-Term Rental (STR) industry, including trust accounting, owner statements, and merchant processing reconciliations.

Key Responsibilities

• Financial Oversight: Manage the full month-end close process for multiple STR clients, ensuring Profit & Loss statements and Balance Sheets are accurate and ready for leadership review.
• Trust Accounting & Owner Statements: Oversee the reconciliation of guest payments, security deposits, and cleaning fees. Ensure owner statements are generated accurately and distributions are processed on time.
• KPI Analysis: Track and report on industry-specific metrics such as RevPAR (Revenue Per Available Room), ADR (Average Daily Rate), and Occupancy rates to provide actionable insights to clients.
• Audit & Compliance: Review the work performed by staff accountants and bookkeepers, ensuring all entries align with US GAAP and client-specific Standard Operating Procedures (SOPs).
• System Integration: Manage data flow between Property Management Systems (PMS) like Guesty, Hostaway, or Streamline and accounting platforms (QuickBooks Online/NetSuite).
• Client Communication: Serve as the primary point of contact for financial inquiries, explaining variances and providing clarity on financial performance during monthly reviews.
  
  

• Industry Experience (MANDATORY): At least 4+ years of direct experience as an Accountant or Senior Accountant specifically within the US Vacation Rental / Short-Term Rental (STR) industry.
• Accounting Foundation: Bachelor’s degree in Accounting or Finance. A solid understanding of US GAAP is required.
• Technical Stack: Advanced proficiency in QuickBooks Online and experience with at least one PMS (e.g., Guesty, Hostaway, Streamline, Track).
• Analytical Skills: Expert-level Excel skills (VLOOKUPs, Pivot Tables, data cleaning) for reconciling complex reservation reports.
• English Proficiency: Exceptional written and verbal communication skills (C1/C2 level) for direct client interaction.
• Growth Mindset: Ability to work in a fast-paced environment and adapt to new technologies and client workflows quickly.
  
  

• Competitive Compensation: Fixed monthly payment in US Dollars.
• Performance Incentives: Quarterly bonuses based on performance and quality metrics.
• Career Path: Bi-annual reviews (July & December) with opportunities to transition into a Senior Controller or Vertical Lead role.
• Flexibility: 100% remote work with a supportive global culture.
• Time Off: 10 paid national holidays per year and unlimited PTO after 6 months of tenure.