Sr. Controller (Vacation Rental Industry)
Howard · United States
- Hybrid
- Contract
- $150,000 / year
- United States
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Job highlights
- Lead financial reporting for Short Term Rental clients.
- Manage and mentor a remote accounting team.
- Oversee complex trust and owner fund accounting.
- Drive month-end close and client financial advisory.
- Scale processes for rapid vertical growth.
About the role
Senior Controller, Short Term 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).
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."
Key skills/competency
- Senior Controller
- Short Term Rentals (STR)
- US GAAP
- Trust Accounting
- Client-Facing Professionalism
- QuickBooks Online
- NetSuite
- Sage Intacct
- Streamline
- Guesty
Skills & topics
- Senior Controller
- Accounting
- Finance
- Short Term Rentals
- STR
- US GAAP
- Trust Accounting
- Property Management
- Hospitality
- Financial Reporting
- Team Management
- Client Relations
- QuickBooks Online
- NetSuite
- Sage Intacct
- Streamline
- Guesty
- Track
- Escapia
- Remote Team
- Startup
- High-Growth
- Investor Relations
- Audit
- Compliance
How to get hired
- Tailor your resume: Highlight STR, US GAAP, and trust accounting expertise.
- Showcase leadership: Emphasize team management and client advisory experience.
- Demonstrate tech skills: List proficiency in QBO, NetSuite, Sage, and PMS tools.
- Emphasize ownership: Provide examples of problem-solving and driving results.
- Ace the interview: Prepare to discuss complex financial scenarios and client interactions.
Technical preparation
Master US GAAP and multi-entity consolidations.,Become expert in trust accounting nuances.,Gain deep experience with STR PMS tools.,Achieve proficiency in QBO, NetSuite, or Sage.
Behavioral questions
Describe a complex financial problem you solved.,How do you lead and mentor a remote team?,Provide an example of driving a month-end close.,How do you ensure accuracy in client reporting?
Frequently asked questions
- What specific accounting software does Howard Financial use for Senior Controller roles?
- For the Senior Controller position, Howard Financial requires proficiency in QuickBooks Online, NetSuite, or Sage Intacct. Familiarity with Property Management System (PMS) tools like Streamline, Guesty, Track, or Escapia is also crucial for managing client data.
- What is the typical career progression for a Senior Controller at Howard Financial?
- Howard Financial emphasizes rapid growth. The Senior Controller role offers a direct path to a Director position, with career advancement primarily limited by individual performance and contribution to the company's scaling efforts.
- How does Howard Financial support remote teams for the Senior Controller role?
- The Senior Controller will lead a remote team. Howard Financial fosters a culture of accountability and precision, suggesting a focus on clear communication, defined expectations, and robust virtual collaboration tools to support remote team management.
- What are the key differences between this Senior Controller role and a 'passive review' position?
- This Senior Controller role is highly hands-on. Unlike passive review positions, you will actively lead a team, drive the month-end close, serve as the primary technical contact for clients, and navigate complex data and accounting structures.
- What makes the Short Term Rental (STR) vertical at Howard Financial unique for a Senior Controller?
- The STR vertical is one of Howard Financial's fastest-growing. This role involves owning financial reporting for sophisticated clients, managing complex trust accounting for owner funds, and dealing with the unique data challenges of PMS integrations within a scaling startup environment.
- How does Howard Financial handle audit and compliance for its clients?
- The Senior Controller is responsible for coordinating external audits and ensuring all tax, sales tax, and regulatory filings are supported by clean documentation. This requires meticulous record-keeping and adherence to US GAAP.
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