Financial Operations Specialist – Multi-Entity AccountingJob Overview
The Dancing Palms is a growing startup, vertically integrated real estate, construction, development, investment, and vacation-rental management company based in Fort Myers Beach. We are seeking a capable, highly organized Financial Operations Specialist to take hands-on ownership of our day-to-day accounting and financial operations across multiple related businesses under the direction of founder as well as our senior CFO advisor.
This role is broader than a traditional bookkeeping position. The Financial Operations Specialist will manage accounts payable and receivable, reconciliations, monthly closes, financial reporting, construction job costing, vacation-rental accounting, and coordination between our operational systems and QuickBooks Online.
The role is currently performed primarily by our founder, with assistance from a senior finance and operations advisor. Both will remain actively involved in providing training, oversight, and support while the new hire progressively assumes ownership of the function.
We are also an AI-first company, actively leveraging modern tools and workflows to improve speed, accuracy, and insight across our operations. The ideal candidate is comfortable using AI tools (such as ChatGPT or similar systems) to assist with analysis, documentation, reconciliation support, and process improvement—and is eager to continue learning and applying AI in practical, day-to-day accounting and financial work.
Primary Responsibilities
· Maintain accurate accounting records across multiple related companies.
· Manage accounts payable, accounts receivable, vendor payments, customer invoicing, and cash receipts.
· Reconcile bank, credit card, trust, intercompany, and balance-sheet accounts.
· Own the monthly accounting close and prepare monthly, quarterly, and annual financial reports.
· Maintain consistent transaction coding, supporting documentation, and accounting procedures.
· Monitor cash positions, upcoming obligations, receivables, and other financial priorities.
· Assist with budgeting, forecasting, cash-flow planning, and management reporting.
· Assist company leadership with investment analysis, project underwriting, scenario analysis, and the development and maintenance of Excel-based financial models.
· Coordinate with company leadership, and when directed with outside accountants and tax advisors, payroll providers, banks, lenders, and other financial partners.
· Help improve financial processes, internal controls, system integrations, and reporting as the businesses grow.
· Leverage AI tools where appropriate to streamline workflows, improve accuracy, and enhance financial analysis and reporting.
Vacation-Rental and Property-Management Accounting
Dancing Palms Vacations uses Guesty and Guesty Accounting to manage booking finances, property expenses, owner statements, trust accounting, and monthly owner payouts. Responsibilities will include:
· Review booking revenue, fees, taxes, refunds, adjustments, and property-level expenses.
· Reconcile Guesty Accounting with bank accounts, trust accounts, payment activity, owner statements, and QuickBooks Online.
· Prepare and review monthly owner statements and net owner payouts.
· Process transfers of earned management fees and other company income from the trust account.
· Investigate and resolve discrepancies before statements and payouts are finalized.
· Maintain clear separation between owner funds and company operating funds.
· Ensure the accurate integration of vacation-rental accounting into QuickBooks Online.
Direct Guesty experience is helpful but not required; training will be provided.
Construction Accounting and Job Costing
Dancing Palms Homes uses JobTread for construction management and job costing, integrated with QuickBooks Online. Responsibilities will include:
· Process and track subcontractor and vendor invoices.
· Maintain accurate job costs, cost codes, purchase orders, commitments, allowances, and change orders.
· Verify invoices against contracts, approvals, and completed work.
· Reconcile JobTread project costs with QuickBooks Online.
· Support customer billing, deposits, progress payments, and accounts receivable.
· Prepare job-level budget-versus-actual and cost-to-complete reporting.
· Assist with construction-loan draws and supporting documentation.
· Maintain vendor records, W-9s, insurance documentation, lien waivers, and 1099 information.
· Help establish scalable construction-accounting procedures as the number of active projects grows.
Investment and Development Support
As secondary to core accounting work, working alongside the founder and senior CFO advisor, this person will also provide analytical support for the company’s real estate investment and development activities. Responsibilities may include:
· Maintain and update project pro formas, development budgets, and cash-flow models.
· Assist with investment-property underwriting and project feasibility analysis.
· Model financing structures, construction costs, operating assumptions, refinancing scenarios, and projected investment returns.
· Prepare scenario and sensitivity analyses to support investment and capital-allocation decisions.
· Compare projected results with actual project and operating performance.
· Organize financial information for lenders, investors, partners, and internal decision-making.
This is a supporting responsibility. The successful candidate does not need to arrive as a real estate investment expert but should be highly capable in Excel and interested in developing deeper analytical and modeling skills.
Qualifications
· Demonstrated experience in bookkeeping, accounting operations, or a similar hands-on financial role.
· Strong proficiency with QuickBooks Online.
· Solid understanding of double-entry bookkeeping and accrual accounting.
· Experience with accounts payable, accounts receivable, reconciliations, general-ledger maintenance, and monthly closes.
· Strong Excel skills, including the ability to work confidently with formulas, linked schedules, financial models, and data analysis.
· Exceptional attention to detail and ability to identify and resolve discrepancies.
· Ability to manage recurring deadlines across multiple companies and operating systems.
· Sound judgment when working with confidential financial information.
· Clear communication skills and a collaborative, service-oriented approach.
· Comfort learning new technology and improving existing processes.
· Familiarity with, and enthusiasm for, using AI tools to enhance productivity, analysis, and workflow efficiency.
Preferred Experience
· Multi-entity accounting.
· Construction accounting, job costing, or construction-loan draws.
· Vacation-rental, hospitality, property-management, or trust accounting.
· Real estate investment analysis, project underwriting, or financial modeling.
· JobTread, Guesty, or comparable industry-specific systems.
· Payroll administration, 1099 reporting, and coordination with outside accountants.
· Bachelor’s or associate degree in accounting, finance, business, or a related field.
Equivalent practical experience is equally valued. A CPA is not required.
What Success Looks Like
Within the first several months, the successful candidate will become proficient in our systems and recurring workflows, establish reliable monthly reporting, and progressively transition day-to-day financial operations from the founder into a well-organized and documented process.
Over time, this person should become the central owner of financial operations across the Dancing Palms companies, with strategic oversight and support from company leadership. The role also offers an opportunity to develop meaningful experience in real estate investment, construction, development, financial modeling, and applied AI-enabled financial operations.
Compensation
$55,000–$70,000 annually, depending on experience, plus benefits.
Candidates with particularly strong construction-accounting, multi-entity, systems-integration, real estate financial-modeling, or AI-enabled workflow experience may be considered above this range.
About The Dancing Palms
The Dancing Palms is building an integrated real estate platform encompassing vacation-rental management, residential construction, property development, design, and investment. We combine local market expertise with thoughtful design, disciplined operations, and technology to create exceptional homes, investments, and guest experiences in Fort Myers Beach.
We value people who take ownership, solve problems proactively, embrace technology (including AI), and care deeply about getting the details right.
Pay: $55,000.00 - $70,000.00 per year
Benefits:
- 401(k)
- Dental insurance
- Health insurance
- Paid time off
Application Question(s):
- Please briefly describe your role in the monthly accounting close at your current or most recent employer. Which parts did you personally perform?
- How many years of experience do you have with construction accounting, job costing, construction draws, or project-level cost reporting?
- Do you have experience with any of the following: multi-entity accounting, property-management accounting, trust accounting, hospitality accounting, or construction accounting? Please briefly describe.
Experience:
- Quickbooks: 2 years (Required)
- core accounting (reconciliations, A/P & A/R, GL, closing): 2 years (Required)
Language:
Ability to Commute:
- Fort Myers Beach, FL 33931 (Preferred)
Work Location: Hybrid remote in Fort Myers Beach, FL 33931
