About Howard Financial

Howard Financial is a full-service back-office solution for companies and entities 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 60 professionals supports ~40 clients across a diverse range of industries. We recently reached $5M of contracted ARR and are growing rapidly (over 150% MRR growth YTD).

About the Role

Howard is seeking an experienced and strategic Controller to lead our Property Accounting team and oversee financial operations for our Vacation Rental (VR) and Homeowners Association (HOA/HOAS) clients. This role is responsible for multi-entity financial management, team leadership, and ensuring accuracy, transparency, and compliance across a fast-growing portfolio.

You will guide a team of accountants, partner closely with operations, and deliver high-level financial insights that drive better owner satisfaction and property performance.

What You’ll Lead & Deliver

Team Leadership

Manage, mentor, and develop a team of property accountants and specialists.

Establish best practices, workflows, and quality controls to ensure accurate and timely reporting.

Support training and onboarding for new team members and new property portfolios.

Financial Management

Oversee full-cycle accounting for a multi-property VR/HOA portfolio (AP, AR, GL, bank reconciliations).

Review and approve monthly financials, owner statements, and HOA board packages.

Ensure proper allocation of income, expenses, reserves, and capital project costs.

Lead budgeting, forecasting, variance reporting, and revenue analysis.

Vacation Rental (VR) Accounting

Oversee revenue recognition, owner payouts, occupancy tax filings, and commission calculations.

Partner with VR operations teams to streamline financial communication and reporting.

Monitor property performance and provide financial insights to owners and leadership.

HOA/HOAS Accounting

Oversee assessment billing, collection cycles, reserve funding, and special assessments.

Ensure compliance with governing documents, accounting standards, and association regulations.

Support HOA boards with reporting, financial presentations, and audit preparation.

What You Bring

• Bachelor’s degree in Accounting, Finance, or related field (CPA preferred).
• 5+ years of property accounting experience, including VR and/or HOA/HOAS.
• Proven experience leading accounting teams in a multi-entity environment.
• Expert knowledge of GAAP and property financial operations.
• Strong proficiency in property management systems (Buildium, AppFolio, Yardi, or similar).
• Excellent communication skills with the ability to support owners, boards, and internal teams.
• Strategic mindset, strong analytical skills, and exceptional attention to detail.