Regional Controller in Bradenton, Florida at Prime Vacations

Regional Controller
Company: Prime Vacations, a subsidiary of StayTerra Vacations
Location: Bradenton, Florida (Tampa area). In office role

Reports to: Prime Vacations COO with a dotted line to the StayTerra Corporate Controller for functional responsibilities

Compensation & Benefits: We offer a competitive salary commensurate with experience, along with a comprehensive benefits package that may include medical, dental, and vision insurance, retirement savings plans, paid time off, paid holidays, and opportunities for professional development.

Position Summary
The Regional Controller will play a critical leadership role in overseeing the accounting and financial reporting operations of Prime Vacations, a vacation home rental business with properties on the Gulf Coast of Florida. This role is responsible for ensuring timely and accurate financial reporting, maintaining a strong control environment, supporting operational decision-making, owning the local budget and forecast, and partnering with the Corporate Finance team to drive process improvements across the organization.
As StayTerra continues to build a best-in-class shared services organization, this position will play an integral role in standardizing accounting processes, supporting systems integration, and providing financial leadership across multiple operating companies within the portfolio. The ideal candidate is a hands-on leader who thrives in a fast-paced environment and can balance technical accounting expertise with operational partnership.
Key Responsibilities
• Lead and manage the monthly close processes to ensure timely and accurate financial reporting
• Ensure compliance with U.S. GAAP, internal accounting policies, and established internal controls
• Directly manages the Assistant Controller and provides strategic leadership for the accounting function. The finance team also includes an Accounting Manager, General Ledger Accountant, Accounts Payable Manager, two Accounts Payable Specialists, and an outsourced team responsible for bank account reconciliations.
• Cash management including liquidity tracking and oversight of operating cash across all business lines.
• Oversee and manage integrations and data integrity between the ERP system (Sage Intacct) and the PMS (Track)
• Ensure all balance sheet reconciliations are prepared, reviewed, and completed prior to close deadlines
• Partner with cross-functional teams to resolve accounting issues and support operational initiatives
• Identify opportunities to enhance processes, improve efficiencies, and strengthen controls
• Develop, document, and maintain standardized accounting procedures (SOPs) and ensure appropriate cross-training within the accounting function.
• Managing an integrated financial technology ecosystem, including Sage accounting software, Track Property Management, Ramp (accounts payable and expense management), JPMorgan banking interfaces, and Track/Sage API integrations.
• Develop a strong understanding of the PMS to support and back up the Track leader as needed
• Lead the monthly financial review presentation
• Support audits and provide required documentation and analysis as needed
• Support local and corporate finance in researching and understanding budget variances
• Partner with operations and corporate FP&A to develop the annual budget and quarterly reforecasts
• Lead, mentor, develop, and evaluate the regional accounting team.
• Establish accountability, training, and succession planning within the department.
• Foster a culture of continuous improvement, collaboration, and customer service.
• Support acquisitions, integrations, system implementations, and other strategic initiatives as assigned
Additional Responsibilities (Trust accounting, PMS, AR, Deposits & Owner Accounting)
• Knowledge of trust accounting principles and experience managing owner and guest funds in a property management or vacation rental environment preferred
• Ensure accurate recording of revenue, owner due to/from balances, and advanced deposits from Track PMS in Sage Intacct. Oversee reconciliation to ensure data integrity and completeness
• Oversee the owner statements process – draft  operational review  finalize distribute to owners  settlement
• Oversee undeposited funds and ensure proper tracking, reconciliation, and timely resolution

Qualifications & Credentials
• 5–7 years of Controller experience or equivalent accounting leadership role
• Bachelor's degree in Accounting, Finance, or a related field required; MBA and/or CPA designation preferred
• Knowledge of U.S. GAAP and accounting best practices
• Comfortable with identifying and improving control weaknesses
• Skilled at assessing control gaps and implementing effective remediation
• Proven experience managing and developing team members
• Strong organizational skills with the ability to meet tight deadlines
• Experience in the travel, hospitality, or property management industry is a plus
• Experience with property management systems (Track PMS, preferred)
• Microsoft 365 experience, especially Microsoft Excel (minimum intermediate proficiency)
• Sage Intacct experience a plus
• Experience with owner accounting, including owner statements and distributions, preferred
• Experience working within a private equity-backed organization or other fast-paced, high-growth environment preferred.
• This position requires approximately 10%–15% travel, primarily for meetings and company events. Travel schedules may vary based on business needs.
• This role requires light physical activity, including sitting, standing, walking, and using a computer for extended periods. Occasional lifting or carrying of items weighing up to 20 pounds may be required.
Equal Opportunity Employer
We are an Equal Opportunity Employer and are committed to fostering an inclusive workplace. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, veteran status, or any other protected characteristic under applicable federal, state, or local law.