Controller / Senior Bookkeeper (Small Business & Fractional CFO Experience)

Job Summary

We are seeking a highly organized, detail-oriented Controller / Senior Bookkeeper with strong small business financial management experience and exposure to CFO-level financial planning and strategy. This individual will oversee day-to-day accounting operations while serving as a trusted financial partner to leadership across multiple growing businesses.

The ideal candidate is comfortable rolling up their sleeves with bookkeeping and reconciliations while also providing meaningful financial insights, cash flow forecasting, budgeting, and strategic recommendations.

Duties

• Manage full-cycle accounting processes including general ledger reconciliation, accounts payable and receivable, and bank account management using software such as QuickBooks, Xero, or Sage.
• Prepare and analyze financial statements, reports, and forecasts aligned with GAAP (Generally Accepted Accounting Principles), IFRS (International Financial Reporting Standards), and other regulatory standards.
• Conduct balance sheet reconciliations, account analysis, and ensure accuracy of debits & credits across all accounts.
• Oversee payroll processing, cash management, and budgeting activities to optimize financial resources.
• Ensure compliance with SOX (Sarbanes-Oxley Act), governmental regulations, and non-profit accounting standards where applicable.
• Lead or assist with regulatory reporting requirements for clients in various sectors including non-profit organizations and government entities.
• Perform technical accounting research on complex transactions such as revenue recognition or lease accounting; prepare detailed financial report writing for stakeholders.
• Support clients with financial management strategies including forecasting, account reconciliation, and internal controls implementation.

Qualifications

• Proven experience in accounting roles with a focus on small business bookkeeping or fractional CFO responsibilities.
• Strong knowledge of GAAP, IFRS, SOX compliance, governmental accounting, and non-profit accounting standards.
• Proficiency in accounting software such as QuickBooks, Xero, Sage, or similar platforms; familiarity with financial software integrations is a plus.
• Demonstrated expertise in balance sheet reconciliation, account analysis, double entry bookkeeping, and general ledger management.
• Experience with financial concepts including budgeting, forecasting, cash flow management, and financial analysis.
• Knowledge of regulatory reporting requirements for various sectors; ability to interpret complex financial regulations.
• Excellent communication skills for preparing clear financial reports and collaborating with clients or internal teams.
• Strong technical accounting skills including understanding of debits & credits, account reconciliation procedures, and internal controls. Join us to leverage your accounting expertise in a vibrant environment that values precision, strategic thinking, and proactive problem-solving!

Pay: $20.00 - $50.00 per hour

Work Location: Hybrid remote in Chicago, IL 60611