Sr. Controller

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 Youll 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 structuresensuring 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 1000 properties.

• Audit & Compliance: Coordinate external audits and ensure that all tax sales tax and regulatory filings are supported by clean documentation.

Ideal Candidate

• 710 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 dont 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 speedyour career path to Director is limited only by your performance.

• Transparent Culture: Clear expectations clean scopes and no corporate fluff.