A growing professional services organization in Chicago is seeking a detail-oriented Office Manager/Bookkeeper to join their team. This hands-on role offers a salary of $75,000–$100,000 dependent on experience and the opportunity to take ownership of day-to-day accounting operations while also supporting key employee and business functions. The position is ideal for someone who enjoys working across multiple areas of a business and wants to play an important role in keeping financial and operational processes organized and running smoothly. The successful candidate will be comfortable managing recurring accounting responsibilities, partnering with leadership, and handling sensitive employee-related matters with discretion. This is a highly visible opportunity for someone who is proactive, organized, and interested in making an impact within a growing organization. The company offers a competitive benefits package, including health insurance, paid time off, and professional development opportunities, along with a collaborative and entrepreneurial work environment. Responsibilities of the Office Manager/Bookkeeper: Oversee daily accounting activities, including payroll, bookkeeping, invoice processing, credit card payments, and accounts payable. Maintain accurate financial records in QuickBooks, complete monthly bank and credit card reconciliations, and assist with financial reporting. Monitor incoming and outgoing funds, including commissions, deposits, wires, reimbursements, and other financial transactions. Prepare invoices, W-9s, receipts, and other financial documentation while assisting with tax-related items and outside accounting partners. Manage company health insurance administration and assist with business insurance policies, renewals, and related employee questions. Coordinate employee onboarding and offboarding alongside the Office Coordinator, including paperwork, benefits enrollment, system access, and personnel records. Partner with leadership on financial and operational priorities, special projects, process improvements, and initiatives that support the organization's continued growth. Qualifications of the Office Manager/Bookkeeper:7–10 years of experience in accounting, bookkeeping, or a related field with increasing levels of responsibility. Strong understanding of accounting fundamentals, financial reporting, reconciliations, accounts payable, accounts receivable, and month-end processes. Experience handling payroll and HR-related administration, with the ability to manage confidential employee information appropriately. Proficiency with Microsoft Excel, QuickBooks, and other accounting or financial software; experience with Bill.com is a plus. Highly organized and detail-oriented with the ability to manage recurring deadlines and multiple priorities without losing accuracy. Strong written and verbal communication skills with a proactive, collaborative, and solutions-oriented approach. Ability to work independently in a fast-paced, entrepreneurial environment; experience in real estate, professional services, or a small business setting is a plus. P-10
