Sr. Controller (Vacation Rentals)

Sr. Controller (Vacation Rental Industry) (EST time zone aligment - 100% remote)

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).

We are looking for a high-caliber Senior Controller to lead one of our fastest-growing Short Term Rental (STR) verticals. You will be the financial owner of a portfolio of sophisticated clients, ensuring that every balance sheet is bulletproof and every report is investor-ready.

This is not a "passive review" role. You will lead a team of Senior Accountants, Accountants, and Bookkeepers, driving the month-end close process and serving as the primary technical point of contact for our clients' leadership teams. You must be comfortable navigating messy data, complex trust accounting structures, and the fast-paced nature of a scaling startup.

What You’ll Do

• Portfolio Leadership: Own the 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 the 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."