Part-Time Bookkeeper / Accountant (Full-Charge)

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

Position Summary

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.

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 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

Required Qualifications

• 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)

Preferred 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

Reporting & Working Relationships

• Reports directly to the owner

• Works alongside our outside accounting firm, which handles tax preparation and filing

Physical Requirements

• Ability to work at a computer for extended periods

• Ability to maintain regular attendance on the scheduled in-office workday(s)