Location: 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
We are seeking a detail-oriented, dependable, and discreet Part-Time Full-Charge Bookkeeper/Accountant to manage the day-to-day financial operations of three commonly-owned small businesses operating in highly regulated, confidentiality-sensitive fields:
A Social Security disability business (handles claimant PII and works to Social Security Administration standards)
A Medicare insurance agency
A law practice (maintains attorney client trust / IOLTA accounts)
This is an in-office role, approximately one to two full days per week. The work is performed primarily in QuickBooks Online, and the right candidate will work independently to keep the books accurate, current, and audit-ready, and will prepare financials for handoff to our outside accounting firm. Payroll, sales/use tax, and tax preparation are handled externally and are not part of this position.
The ideal candidate has full-charge bookkeeping experience, has worked with attorney trust/IOLTA accounts (including three-way reconciliation), understands the discretion required when handling sensitive personal and government-regulated information, and can be trusted to work independently with minimal supervision.
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 our 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
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 (this role has full access to financial records and sensitive information)
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
Reports directly to the owner
Works alongside our outside accounting firm, which handles tax preparation and filing
Ability to work at a computer for extended periods
Ability to maintain regular attendance on the scheduled in-office workday(s)
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