Sr. Controller (Vacation Rental Industry)
Howard · Pennsylvania, United States
- Hybrid
- Contract
- $150,000 / year
- Pennsylvania, United States
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Job highlights
- Lead financial reporting for STR clients.
- Manage and mentor a remote accounting team.
- Oversee complex trust accounting structures.
- Drive month-end close and client communication.
- Scale processes for rapid company growth.
About the role
About Howard Financial
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).
Job Summary
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
- Own the end-to-end financial reporting for a vertical of Short Term Rental clients, ensuring US GAAP compliance and institutional-grade accuracy.
- Lead, mentor, and review the work of a remote team (Senior Accountants to Bookkeepers), fostering a culture of accountability and precision.
- Manage and reconcile complex "owner funds" and trust accounting structures—ensuring the separation of client funds is impeccable.
- Drive a tight month-end close process, identifying and resolving discrepancies in PMS data (Streamline, Guesty, Track, etc.) vs. General Ledgers.
- Act as the 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 from 100 to 1,000+ properties.
- Coordinate external audits and ensure that all tax, sales tax, and regulatory filings are supported by clean documentation.
Ideal Candidate Profile
- 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 is a must.
- Comprehensive knowledge of US GAAP and multi-entity consolidations.
- You understand the nuances of managing funds on behalf of property owners.
- You can hold your own in a room (or Zoom) with CEOs and PE-investors.
- Proficiency in QuickBooks Online, NetSuite, or Sage Intacct, and expert-level comfort with PMS tools, specifically Streamline, Guesty, Track, or Escapia.
- You don't just find problems; you "chase" them until they are resolved.
- 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."
Key skills/competency
- Senior Controller
- Short Term Rentals
- US GAAP
- Trust Accounting
- Client-Facing
- Team Management
- Month-End Close
- Financial Reporting
- Process Scaling
- Leadership
Skills & topics
- Senior Controller
- Accounting
- Finance
- Short Term Rentals
- STR
- US GAAP
- Trust Accounting
- Property Management
- Hospitality
- Team Leadership
- Month-End Close
- Financial Reporting
- QuickBooks
- NetSuite
- Sage Intacct
- Streamline
- Guesty
- Track
- Remote Team
How to get hired
- Tailor your resume: Highlight STR, US GAAP, and leadership experience.
- Showcase client-facing skills: Emphasize communication with CEOs and investors.
- Demonstrate technical proficiency: List experience with QuickBooks, NetSuite, and STR PMS tools.
- Emphasize ownership mentality: Use examples of problem-solving and driving resolution.
- Prepare for technical interviews: Expect questions on US GAAP and trust accounting nuances.
Technical preparation
Master US GAAP and consolidations.,Practice trust accounting problem-solving.,Become expert in STR PMS software.,Prepare for complex P&L analysis.
Behavioral questions
Describe a complex accounting problem you solved.,How do you ensure accuracy in financial reporting?,How do you manage and mentor a remote team?,How do you handle client objections or concerns?
Frequently asked questions
- What is Howard Financial's focus as a company?
- Howard Financial provides comprehensive back-office solutions, including bookkeeping, payroll, and specialized reporting, for high-growth companies, particularly those in the vacation rental industry.
- What is the primary responsibility of the Senior Controller at Howard Financial?
- The Senior Controller will be the financial owner of a portfolio of Short Term Rental clients, ensuring financial accuracy, US GAAP compliance, and investor-ready reporting, while leading a team of accountants.
- What industry experience is required for this Senior Controller role?
- Deep experience in Short Term Rentals (STR), Property Management, or the Hospitality industry is a mandatory requirement for this position.
- What technical accounting skills are essential for a Senior Controller at Howard?
- Expert knowledge of US GAAP, multi-entity consolidations, and intricate trust accounting structures, especially concerning owner funds, is crucial.
- What kind of team will the Senior Controller lead at Howard Financial?
- The Senior Controller will lead a remote team composed of Senior Accountants, Accountants, and Bookkeepers, requiring strong management and mentoring skills.
- What software and systems should a candidate be proficient in for this role?
- Proficiency in accounting software like QuickBooks Online, NetSuite, or Sage Intacct, and expert-level familiarity with STR Property Management Systems (PMS) such as Streamline, Guesty, or Track is expected.
- How does Howard Financial support career growth for its employees?
- Howard Financial emphasizes rapid growth and offers significant opportunities for career advancement, with a clear path to Director roles based on individual performance.
- What makes the work environment at Howard Financial unique?
- Howard Financial fosters a transparent culture with clear expectations and scopes, focusing on high-level complexity and providing 'True Ownership' where employees act as the 'CEO of their vertical.'
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