Part-Time QBO Bookkeeper — Weekly & Monthly Accounting Maintenance Cloud9 / Short-Term Rental ops

Part-Time QBO Bookkeeper — Weekly & Monthly Accounting Maintenance (Cloud9 / Short-Term Rental Operations) About the Role We're a Chicago-based short-term rental company managing multiple luxury apartment buildings across the city. We're looking for a detail-oriented QBO bookkeeper to own our weekly and monthly accounting tasks and keep our books clean, current, and ready for review at all times. This is a part-time, ongoing remote role. You'll work independently — we just need someone who knows QBO inside out and doesn't need hand-holding. What You'll Do Weekly Review and categorize bank and credit card feeds — match transactions to invoices, receipts, or bills and assign new expenses to the correct accounts Make sure all invoices from our booking platforms and internal billing are properly synced and recorded in QBO Apply incoming payments (ACH, check, card) to open invoices so nothing duplicates Send reminders for overdue accounts Upload and match receipts and vendor invoices via QBO Receipt Capture Record new vendor bills and schedule weekly payments Review and approve contractor timesheets before syncing to QBO Payroll — confirm job and class cost allocations are correct What You'll Do Monthly Reconcile all bank accounts, credit cards, and loan accounts against monthly statements — we expect $0.00 discrepancy Clear out any transactions that have been sitting uncleared for 30–60+ days Clean up anything stuck in Uncategorized Expenses, Uncategorized Income, or Ask My Accountant Review the balance sheet for anything off — negative liabilities, unexpected balances, anything that doesn't look right Reconcile payroll liabilities and confirm every payroll withdrawal matches wages, taxes, and deductions logged in QBO You're a Good Fit If You: Have 2+ years working in QBO (QuickBooks Online) — not just familiar, you actually live in it Have experience with short-term rental, hospitality, or property management accounting (a plus but not required) Are comfortable with multiple entities and bank accounts Can turn things around quickly without follow-up Communicate clearly and flag issues proactively Details Remote / flexible hours Estimated 5–8 hours/week Ongoing engagement — we're not looking for a one-time project US-based or Latin America preferred (we operate in both) To Apply Please include your QBO experience, any relevant industry background, and your hourly rate. Bonus points if you share a sample reconciliation or cleanup project you've done.