About Howard Financial
Howard Financial is a tech-forward outsourced accounting and finance firm built for fast-growing US companies. Founded in 2023, we’ve grown to a team of ~100 professionals supporting roughly 75 clients, with over 200% year-over-year growth ($6M ARR).

We serve clients across four specialized verticals: Vacation Rental, Hospitality, Consumer & E-Commerce, and Development & Real Estate. This industry focus means our teams build deep expertise in the businesses they support, rather than acting as generalist bookkeepers.

We operate with high autonomy, low red tape, and modern technology. Our remote team is built around ownership, continuous improvement, and a genuine interest in using tools and automation to do better work. As we keep scaling, there is real room to grow your scope and your career with us.

The Role
We are hiring a proactive, tech-forward Controller to join our Short-Term Rental (STR) & Hospitality vertical.

You will own the month-end close and financial reporting for a portfolio of clients. You will review the work of accountants and bookkeepers and be a trusted point of contact for client stakeholders. You’ll work closely with senior finance leadership, and the role is a strong fit for someone ready to step into broader ownership. You’ll thrive here if you enjoy solving complex accounting problems, getting trust accounting right, and making processes cleaner and more efficient.

Deep STR experience is ideal, but we welcome strong Hospitality candidates who are tech-savvy fast learners.

What You’ll Do

• Close & Reporting: Own the month-end close and US GAAP financial reporting for a portfolio of STR/Hospitality clients, ensuring accuracy and on-time delivery.
• Review & Mentorship: Review reconciliations, journal entries, and financials prepared by accountants and bookkeepers, giving clear feedback that helps them grow.
• Trust Accounting: Manage owner-fund and trust accounting, including reconciliations and owner statements, with a high degree of precision.
• Client Support: Serve as a key point of contact for client stakeholders. Explain financial results, P&L trends, and cash flow, and escalate strategic topics to senior leadership.
• Process Improvement: Identify inefficiencies, strengthen controls, and help standardize workflows as client portfolios grow.

What We’re Looking For

• Experience: 5+ years in accounting, including 2+ years in a Controller, Assistant Controller, or Accounting Manager role.
• Domain Knowledge: Experience in Short-Term Rentals, Property Management, or Hospitality.
• Technical Accounting: Solid command of US GAAP and trust accounting. Multi-entity experience is a plus.
• Tech-Forward Mindset: Proficient in QBO, NetSuite, or Sage Intacct, plus PMS software (Guesty, Streamline, Track, or similar).
• Ownership & Communication: A self-starter who digs into messy data, manages multiple clients and deadlines, and communicates clearly with clients and internal teams.
• Language: Fluent spoken and written English.

What Success Looks Like

First 30 days

• Get up to speed on Howard’s close process, tools, and review standards.
• Learn your client portfolio: entity structures, trust accounting setup, PMS integrations, and reporting calendar.
• Build working relationships with your accountants, bookkeepers, and the senior finance leadership you’ll partner with.

First 60 days

• Run the month-end close for your portfolio with growing independence.
• Review your team’s reconciliations and financials, with clear and consistent feedback.
• Spot your first process gaps or control weaknesses and propose fixes.

First 90 days

• Fully own close and reporting for your portfolio: on time, accurate, and review-ready.
• Act as a trusted point of contact for client stakeholders on financial results and trust accounting questions.
• Lead at least one process improvement or standardization initiative within the vertical.

Ongoing, we expect you to:

• Deliver a clean, on-time close every month with minimal rework.
• Keep owner-fund and trust balances fully reconciled and audit-ready.
• Raise risks and issues early instead of waiting to be asked.
• Help your team level up through review, coaching, and documentation.
• Take ownership: work independently, prioritize across clients, and solve problems without hand-holding.

Schedule
This is a full-time role with required availability Monday–Friday, 9 AM–5 PM EST, to align with our US-based clients and internal team.

What We Offer

• 100% Remote: Work from anywhere as an independent contractor.
• Quarterly Bonus: Performance-based bonuses paid every quarter.
• Periodic Reviews: Regular performance reviews to recognize growth and adjust compensation.
• PTO + 10 National Holidays: Paid time off plus ten recognized national holidays per year.
• Real Growth Opportunity: A clear path to expand your scope toward Senior Controller as Howard and the STR & Hospitality vertical keep scaling.