Financial Manager

Bookkeeper (Multi-Entity / Executive Support)

Location: Flexible | In Person or Hybrid Options Available

Full-Time

About the Role

We are seeking a highly organized and detail-oriented Bookkeeper to support a group of executive partners who own and operate a diverse portfolio of businesses across multiple industries.

This role is ideal for someone who thrives in a dynamic environment and is experienced in managing multiple sets of books, accounts, and financial workflows simultaneously.

Position Overview

The Bookkeeper will be responsible for maintaining accurate financial records, supporting reporting and cash flow visibility, and ensuring consistency across multiple business entities.

This position requires a high level of discretion, organization, and the ability to bring structure to a fast-moving, entrepreneurial environment.

Key Responsibilities

Multi-Entity Financial Management

• Maintain and manage books across multiple business entities
• Record and categorize transactions with accuracy and consistency
• Reconcile bank accounts, credit cards, and payment platforms
• Ensure clean, up-to-date financial records across all accounts

Accounts Payable & Receivable

• Manage vendor payments, invoices, and due dates
• Issue invoices and track incoming payments
• Monitor outstanding balances and follow up as needed

Reporting & Financial Visibility

• Prepare monthly financial reports (Profit & Loss, cash flow summaries, etc.)
• Assist with budget tracking and financial forecasting
• Provide leadership with clear, organized financial insights

Payroll & Compliance Support

• Assist with payroll processing and tracking (if applicable)
• Prepare and organize documentation for CPAs and tax filings
• Ensure financial records are audit-ready and compliant

Systems & Process Optimization

• Help streamline accounting workflows across multiple entities
• Maintain organized digital filing systems and documentation
• Identify inefficiencies and recommend improvements

Qualifications

• 2+ years of bookkeeping or accounting experience (multi-entity experience preferred)
• Proficiency in QuickBooks (Online preferred) or similar platforms
• Strong understanding of accounting fundamentals and reconciliations
• Experience managing multiple accounts, entities, or clients
• High level of attention to detail and accuracy
• Strong organizational and time management skills
• Ability to handle confidential financial information with discretion

Preferred Experience

• Experience working with entrepreneurs, partnerships, or holding companies
• Familiarity with multiple revenue streams (events, retail, service-based, etc.)
• Experience integrating payment processors (Stripe, Shopify, etc.)
• Comfortable working in a fast-paced, evolving business environment

What We’re Looking For

• A proactive, systems-oriented thinker who can bring clarity to complexity
• Someone who is reliable, consistent, and detail-driven
• Ability to work independently while maintaining strong communication
• Comfortable managing priorities across multiple businesses

Compensation

• Competitive hourly rate based on experience
• Flexible schedule
• Opportunity to grow into a larger financial or operations role as the portfolio expands

How to Apply

Please submit:

• Your resume
• A brief overview of your experience managing multiple sets of books
• Accounting software you are proficient in
• (Optional) References or sample reports

Pay: From $25.00 per hour

Expected hours: 40.0 per week

Work Location: Hybrid remote in Brooksville, FL 34601