Part Time Bookkeeper/Accountant

About the role

Part-Time Bookkeeper / Accountant (Full‑Charge) – Chicago, IL (in‑office only). Schedule: 2‑3 full days per week (8 hours per day) with flexible scheduling. Compensation: $35–$45 per hour, based on experience. Classification: open to either W‑2 employee or 1099 independent contractor. The position manages day‑to‑day financial operations for three commonly‑owned small businesses (a Social Security disability claim‑handling firm, a Medicare insurance agency, and a law practice maintaining attorney‑client trust/IOLTA accounts) using QuickBooks Online. The role keeps the books accurate, current, and audit‑ready, prepares financials for handoff to an outside accounting firm, and ensures strict confidentiality of sensitive personal, government‑regulated, and client information. Payroll, sales/use tax, and tax preparation are handled externally.

Responsibilities

• Maintain accurate, current financial records for three small companies in QuickBooks Online
• Record and categorize income and expenses across all three entities
• Reconcile bank and credit card accounts monthly
• Perform three‑way reconciliation of attorney trust (IOLTA) accounts, maintain per‑client ledgers, and keep documentation audit‑ready
• Process accounts payable and accounts receivable as needed
• Maintain vendor records and payment schedules
• Track activity involving related/commonly‑owned entities accurately
• Prepare month‑end and year‑end financial statements, including profit & loss statements and balance sheets
• Compile and organize year‑end financials and supporting documentation for the outside accounting firm
• Coordinate directly with the outside accounting firm on tax‑related requests
• Ensure the accuracy, completeness, and integrity of all financial records
• Maintain strict confidentiality of all financial, client, and business information

Requirements

• Associate’s degree in Accounting, Finance, or a related field
• Minimum 2 years of full‑charge bookkeeping/accounting experience
• Strong proficiency with QuickBooks Online
• Demonstrated experience with attorney trust/IOLTA account management, including three‑way reconciliation and client trust ledgers
• Experience working in confidentiality‑sensitive and/or government‑regulated environments (e.g., handling PII, SSA, or healthcare/Medicare‑related records)
• Solid experience with bank reconciliations and general ledger accounting
• Working knowledge of accounts payable and accounts receivable processes
• Proficiency with Microsoft Office and Google Workspace
• Comfort using online banking portals
• Excellent attention to detail and organizational skills
• Ability to work independently with minimal supervision
• Strong communication and problem‑solving skills
• Ability to pass a background check (role has full access to financial records and sensitive information)

Qualifications

• Experience supporting multiple commonly‑owned small businesses
• Experience preparing year‑end documentation and working directly with outside accountants or CPAs
• Familiarity with the recordkeeping and confidentiality standards of legal, insurance, or Social Security practices

Skills

• QuickBooks Online proficiency
• Three‑way reconciliation of IOLTA accounts
• Bank and credit card reconciliation
• Accounts payable and receivable processing
• Microsoft Office and Google Workspace
• Online banking portal navigation
• Attention to detail and organization
• Independent work ethic
• Communication and problem‑solving
• Background‑check eligibility

Pay

$35–$45 per hour, based on experience.

Schedule

2‑3 full days per week (8 hours per day), with flexible scheduling; in‑office only.