BOOKKEEPER - RETAIL & E-COMMERCE

This role is hands-on and operational, requiring strong bookkeeping judgment, consistency, and discipline. You will ensure the books are clean, reconciled, and current while supporting bill payment, invoice processing, and expense monitoring across the team. You will work closely with our external accounting firm to provide all required documentation for tax preparation and year-end close, and partner directly with Ownership to deliver accurate, timely monthly reporting. Part-Time | 8-12 hours/week (up to 20 hours/week during onboarding) Location: Remote or In-Person (Chicago) CORE RESPONSIBILITIES BOOKKEEPING & RECONCILIATION

• Maintain accurate, up-to-date books in QuickBooks (or equivalent)
• Record and categorize all transactions according to established accounting rules
• Perform weekly and monthly bank and credit card reconciliations
• Maintain organized, audit-ready financial records
• Execute monthly close procedures on schedule

ACCOUNTS PAYABLE & BILL PAY

• Process and schedule payment of vendor bills and invoices
• Ensure invoices are properly coded and approved prior to payment
• Maintain bill payment calendars and due-date tracking
• Match invoices to receipts, purchase orders, or delivery confirmations where applicable
• Flag discrepancies, duplicate charges, or missing documentation

EXPENSE MONITORING

• Review and reconcile team expense submissions
• Ensure expenses align with company policies and approved categories
• Monitor recurring subscriptions and operational expenses
• Flag unusual or out-of-policy spending for review

SALES & E-COMMERCE RECONCILIATION

• Reconcile Shopify sales, refunds, discounts, gift cards, and payouts
• Ensure sales data aligns between Shopify and accounting software
• Flag discrepancies promptly

INVENTORY & COGS EXECUTION

• Record inventory purchases and costs following established accounting rules
• Allocate shipping, customs, duties, and restoration costs per defined methodology
• Record Cost of Goods Sold accurately upon sale
• Reconcile inventory balances between accounting software and inventory systems
• Flag missing data or inconsistencies for review

PAYROLL, TAX & COMPLIANCE SUPPORT

• Support payroll processing and reporting
• Execute multi-state sales tax filings on a monthly basis
• Prepare documentation for 1099s and year-end close
• Provide clean, organized records to the external CPA as needed
• Monitor and manage the 401(k) program with ADP

REPORTING

• Deliver standard monthly financial reports, including:
• Profit & Loss
• Balance Sheet
• Cash Flow
• Highlight anomalies, missing invoices, or reconciliation issues

QUALIFICATIONS

• 10+ years of professional bookkeeping experience
• Significant experience with inventory-based businesses (retail, e-commerce, or wholesale)
• Expert proficiency in QuickBooks
• Proven experience reconciling Shopify
• Strong understanding of accounts payable, expense management, and COGS mechanics
• Exceptionally detail-oriented, organized, and reliable
• Comfortable working independently in a remote environment

NICE TO HAVE

• Experience with Airtable or inventory management tools
• Multi-state sales tax experience
• Experience supporting founder-led businesses

TIME COMMITMENT

• Ongoing: 8–12 hours per week
• Occasional peak periods: up to 18 hours per week
• Onboarding period may require additional hours (up to 20 hours per week)

LOCATION

• Remote role (U.S.-based preferred)
• Ability to work asynchronously with a Chicago-based team and within our time zone

COMPENSATION

• Hourly rate: Based on experience

HOW TO APPLY Please send your resume, cover letter, and 3–4 professional references to [email protected]