Bookkeeper & Accounting Assistant Job Chicago Illinois USA,Accounting

Outsourcing Staffing Advantage is a boutique Business Process Outsourcing (BPO) firm specializing in providing high-quality remote professionals to businesses across the United States. We are seeking detail-oriented and organized Bookkeepers & Accounting Assistants to join our talent pool. In this role, you will support clients with day-to-day financial operations, maintain accurate financial records, reconcile accounts, and assist with reporting to ensure the integrity of financial data and compliance with company procedures.

Key Responsibilities

Record and maintain accurate financial transactions in accounting software.
Reconcile bank accounts, credit card statements, and general ledger accounts.
Process accounts payable and accounts receivable transactions.
Prepare and issue invoices, purchase orders, and payment records.
Assist with payroll processing and employee expense reimbursements.
Prepare financial reports and assist with month-end and year-end closing activities.
Maintain organized financial records and supporting documentation.
Monitor outstanding balances and follow up on overdue accounts when required.
Ensure compliance with company policies and accounting standards.
Collaborate with clients and internal teams to resolve financial discrepancies.

Preferred Qualifications

2+ years of experience in bookkeeping, accounting, or a related financial role.
Strong understanding of bookkeeping principles and accounting practices.
Experience using Quick Books Online, Quick Books Desktop, Xero, or similar accounting software.
Proficiency in Microsoft Excel or Google Sheets, including formulas and data organization.
Excellent attention to detail and strong analytical skills.
Ability to manage multiple priorities while maintaining accuracy.
Excellent written and verbal English communication skills.
English proficiency at a C1 level or higher (written and verbal) with a slight to neutral accent.
Availability to work during Eastern Time (ET) business hours
Ability to work independently in a remote environment.
Reliable internet connection and a dedicated home office setup.
Associate’s or Bachelor’s degree in Accounting, Finance, Business Administration, or a related field (preferred but not required).
Experience supporting U.S.

-based businesses.
Familiarity with U.S. GAAP and general accounting principles.
Experience processing payroll using Gusto, ADP, Paychex, or similar payroll platforms.
Experience preparing financial statements and month-end reconciliations.
Familiarity with , Expensify, Stripe, or similar financial management tools.
Experience working remotely with international teams.
Familiarity with AI productivity tools such as ChatGPT, Claude, or Microsoft Copilot for improving workflow efficiency.
Opportunity to work on diverse and exciting projects.
Supportive and collaborative work environment.
Weekly payments.
Weekends off.
Growth opportunities.