Sr. Controller (Vacation Rental Industry)
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Key skills for this role
About the Role
Howard Financial is seeking a Senior Controller to lead a Short Term Rental vertical, overseeing financial reporting, team management, trust accounting, and client advisory. The role requires 7-10+ years of accounting experience, US GAAP expertise, and deep knowledge of the vacation rental industry.
Key Skills for This Role
Responsibilities
- Own end to end financial reporting for a vertical of Short Term Rental clients, ensuring US GAAP compliance
- Lead, mentor, and review the work of a remote team (Senior Accountants to Bookkeepers)
- Manage and reconcile complex owner funds and trust accounting structures
- Drive a tight month end close process, identifying and resolving discrepancies in PMS data vs. General Ledgers
- Act as strategic financial advisor for clients, explaining P&L variances, cash flow projections, and operational health
- Standardize workflows and implement internal controls as the vertical grows
- Coordinate external audits and ensure tax, sales tax, and regulatory filings are supported by clean documentation
Requirements
- 7–10+ years of experience in accounting/finance, with at least 3 years in a Controller or Senior Leadership role
- Deep experience in Short Term Rentals (STR), Property Management, or Hospitality
- Comprehensive knowledge of US GAAP and multi entity consolidations
- Understanding of managing funds on behalf of property owners (trust accounting)
- Proficiency in QuickBooks Online, NetSuite, or Sage Intacct
- Expert level comfort with PMS tools: Streamline, Guesty, Track, or Escapia
- Native level or fully fluent English
Full Job Posting
About Howard Financial
- Howard Financial is a full service back office solution for high growth companies with bookkeeping, payroll, and bespoke reporting needs.
- Founded in 2023, our team of ~100 professionals supports ~75 clients across diverse industries. We recently reached $6M of contracted ARR and are growing rapidly.
What You’ll Do
- Portfolio Leadership: Own end to end financial reporting for a vertical of Short Term Rental clients, ensuring US GAAP compliance and institutional grade accuracy.
- Team Management: Lead, mentor, and review the work of a remote team (Senior Accountants to Bookkeepers), fostering a culture of accountability and precision.
- Trust Accounting Oversight: Manage and reconcile complex 'owner funds' and trust accounting structures—ensuring the separation of client funds is impeccable.
- Month End Mastery: Drive a tight month end close process, identifying and resolving discrepancies in PMS data (Streamline, Guesty, Track, etc.) vs. General Ledgers.
- Client Facing Communication: Act as strategic financial advisor for clients, explaining P&L variances, cash flow projections, and operational health.
- Process Scaling: Standardize workflows and implement internal controls as the vertical grows from 100 to 1,000+ properties.
- Audit & Compliance: Coordinate external audits and ensure that all tax, sales tax, and regulatory filings are supported by clean documentation.
Ideal Candidate
- 7–10+ years of experience in accounting/finance, with at least 3 years in a Controller or Senior Leadership role.
- Industry Expertise: Deep experience in Short Term Rentals (STR), Property Management, or Hospitality is a must.
- US GAAP Expert: Comprehensive knowledge of US GAAP and multi entity consolidations.
- Master of Trust Accounting: You understand the nuances of managing funds on behalf of property owners.
- Client Facing Professionalism: You can hold your own in a room (or Zoom) with CEOs and PE investors.
- System Agnostic & Tech Savvy: Proficiency in QuickBooks Online, NetSuite, or Sage Intacct, and expert level comfort with PMS tools, specifically Streamline, Guesty, Track, or Escapia.
- Ownership Mentality: You don't just find problems; you 'chase' them until they are resolved.
- Native level or Fully Fluent English: Exceptional written and verbal communication is non negotiable.
Nice to Have
- Prior experience in an accounting firm or BPO managing multi client portfolios.
- Experience with institutional or Private Equity backed hospitality clients.
- Advanced data visualization skills (PowerBI, Tableau, or advanced Excel).
Why Howard?
- High Level Complexity: Solve real world financial puzzles for sophisticated US investment platforms.
- True Ownership: You are the 'CEO of your vertical.' We provide the platform; you provide the excellence.
- Rapid Scale: We are growing at record speed—your career path to Director is limited only by your performance.
- Transparent Culture: Clear expectations, clean scopes, and no 'corporate fluff.'
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