Multi-Entity Bookkeeping Specialist

Job Summary: We need a detail-driven Multi-Entity Bookkeeping Specialist to manage the books and compliance for a growing real estate portfolio and an e-commerce brand operating across several LLCs and S corporations. You'll own reconciliations, entity maintenance, payroll setup, and CPA reporting, while coordinating vendor payments and guiding two junior team members. The right fit brings strong US bookkeeping experience, solid knowledge of US entity compliance, and the discipline to keep every account accurate to the penny. Key Responsibilities: Reconcile income and expenses across multiple bank accounts, credit cards, and payment methods to the penny

• Spot and separate personal charges from business transactions across all entities
• Maintain and update the real estate portfolio performance tracker
• Check AI-generated bookkeeping entries for accuracy and fix any miscategorizations
• Prepare and send monthly statements and updates to the CPAKeep the e-commerce business's books separate from the real estate entities
• Maintain annual filings and good standing for all LLCs and S corporations
• Set up and manage payroll registration in two states
• Coordinate with the property manager and contractor, including reviewing and approving payments
• Assign, supervise, and review the work of two interns
• Mandatory Skills: Proven US bookkeeping experience, including managing books for multiple entities at once
• Strong knowledge of US entity compliance, including LLC and S corp annual filings and maintaining good standing
• Experience with multi-state payroll registration and setup
• Advanced account reconciliation skills across multiple accounts and payment platforms
• Strong proficiency in Excel or Google Sheets
• Comfortable assigning, supervising, and reviewing the work of junior team members
• Exceptional attention to detail and accuracy
• Consistent, detail-focused, and able to self-manage
• Strong written communication skills and comfort working asynchronously
• Preferred Skills: Experience with real estate bookkeeping, including rental property income and expense tracking
• E-commerce bookkeeping experience
• Familiarity with cloud accounting software such as QuickBooks Online or Xero
• Experience reviewing or working alongside AI or automated bookkeeping tools
• Experience coordinating with CPAs, property managers, or contractors
• Familiarity with Slack for team communication
• Ability to juggle multiple projects at once

Why Join Us: Join a growing, owner-led business where your expertise directly shapes how the company operates. You'll work closely with a hands-on owner who values accuracy and independence, and an asynchronous communication style lets you manage your own workflow. The role offers real ownership, leadership responsibility, and room to grow as the portfolio expands.