Bookkeeper Jobs in Chicago, IL
Bookkeeper jobs in Chicago are concentrated in the Loop, River North, and the West Loop, with steady demand from professional services firms, healthcare systems, and commercial real estate operators, among the employers actively hiring right now are CDW, CliftonLarsonAllen, and VIVA. See the openings below and apply to the ones that match your experience.
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INTRODUCTION
Cowbell is signalling a new era in cyber insurance by harnessing technology and data to provide small and medium-sized enterprises (SMEs) with advanced warning of cyber risk exposures bundled with cyber insurance coverage adaptable to the threats of today and tomorrow. Championing adaptive insurance, Cowbell follows policyholders’ cyber risk exposures as they evolve through continuous risk assessment and continuous underwriting. In its unique AI-based approach to risk selection and pricing, Cowbell’s underwriting platform, powered by Cowbell Factors, compresses the insurance process from submission to issue to less than 5 minutes. Founded in 2019 and based in the San Francisco Bay Area, Cowbell has rapidly grown, now operating across the U.S., Canada, U.K., and India. This growth was recently bolstered by a successful Series C fundraising round of $60 million from Zurich Insurance. This investment not only underscores the confidence in Cowbell’s mission but also accelerates our capacity to revolutionize cyber insurance on a global scale. With the backing of over 25 prominent reinsurance partners, Cowbell is poised to redefine how SMEs navigate the evolving landscape of cyber threats.
OBJECTIVE
The Senior Accountant is responsible for balance sheet account reconciliations, journal entries, and month-end close deliverables, and for maintaining accurate and well-supported accounting records. You will work across the company's entities, including support for the international entities, and will have the opportunity to expand and grow your role as the company scales.
WHAT YOU WILL DO
- Prepare and maintain clean, current balance sheet account reconciliations, researching and clearing reconciling items rather than carrying them forward
- Reconcile bank statements
- Prepare and post journal entries, including accruals, prepaids, and other adjusting entries, with supporting documentation attached
- Categorize and post transactions in the general ledger
- Conduct month-end and year-end closes to the close calendar
- Prepare intercompany entries and intercompany reconciliations across entities
- Support the monthly close for the international entities (UK, Australia, and India) and review reconciliations prepared for those entities
- Maintain and update accounting records, workpapers, and files so balances are supported and traceable
- Prepare schedules and documents for audits
BASIC QUALIFICATIONS
- Bachelor's degree in accounting or finance required
- 5+ years of relevant accounting experience, with hands-on ownership of balance sheet reconciliations and month-end close
- Multi-entity accounting experience; intercompany and multi-currency exposure preferred
- Insurance industry knowledge and experience preferred
- Experience with NetSuite preferred
- Excellent communication skills, both written and verbal
- Working knowledge of GAAP
- High degree of initiative and independence in completing tasks
- Good problem-solving and time management skills
COMPENSATION
- Pay Transparency: Cowbell is committed to fair and transparent compensation practices. The expected base salary range for this position is $85,000.00-135,000.00 annually. Actual compensation will be determined based on factors such as experience, skills, qualifications, geographic location, and business needs. This position may also be eligible for additional compensation, including bonus/incentive compensation and equity, as applicable. Cowbell also offers a comprehensive health and wellness benefits package.
EQUAL EMPLOYMENT OPPORTUNITY
We are committed to equal opportunity in the terms and conditions of employment for all employees and job applicants without regard to race, color, religion, sex, sexual orientation, age, gender identity or gender expression, national origin, disability, or veteran status. Cowbell is a leading innovator in cyber insurance, dedicated to empowering businesses to always deliver their intended outcomes as the cyber threat landscape evolves. Guided by our core values of TRUE—Transparency, Resiliency, Urgency, and Empowerment—we are on a mission to be the gold standard for businesses to understand, manage, and transfer cyber risk. At Cowbell, we foster a collaborative and dynamic work environment where every employee is empowered to contribute and grow. We pride ourselves on our commitment to transparency and resilience, ensuring that we not only meet but exceed industry standards. We are proud to be an equal opportunity employer, promoting a diverse and inclusive workplace where all voices are heard and valued. Our employees enjoy competitive compensation, comprehensive benefits, and continuous opportunities for professional development. Cowbell is an E-Verify employer. E-Verify is a web-based system that allows an employer to determine an employee's eligibility to work in the US using information reported on an employee's Form I-9. The E-Verify system confirms eligibility with both the Social Security Administration (SSA) and Department of Homeland Security (DHS). For more information, please go to the USCIS E-Verify website.
Cowbell Cyber does not permit the use of AI tools during any stage of our interview process. By submitting your application, you agree to complete all assessments and interviews without the use of generative AI assistance.
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Who's Hiring



Top Industries Hiring
- Technology & Software
- Government & Public Sector
- Banking & Financial Services
- Biotechnology & Pharmaceuticals
Bookkeeper Jobs in Chicago: Frequently Asked Questions
How do I get a bookkeeper job in Chicago?
Targeting employers in the Loop and West Loop gives you the best starting point, where accounting firms, commercial real estate companies, and mid-size professional services firms hire bookkeepers regularly. Familiarity with QuickBooks, Sage, or industry-specific ERP systems used in Chicago's manufacturing and healthcare sectors adds real weight to an application. Networking through the Illinois CPA Society's Chicago chapter also connects candidates with firms that post openings before they go public.
Which companies hire bookkeepers in Chicago?
Chicago bookkeeper roles are posted by CDW, CliftonLarsonAllen, and VIVA and others right now, based on current listings on Migrate Mate as of September 2026. Chicago's mix of large healthcare networks, commercial real estate firms, and regional accounting practices means openings appear across a wide range of employer sizes and industries.
Are there remote bookkeeper jobs in Chicago?
Yes, though availability depends heavily on the role: transactional bookkeeping tied to on-site operations tends to stay in-office, while accounts payable reconciliation and financial reporting work more readily goes remote. About 87% of bookkeeper openings tied to Chicago are remote or hybrid as of September 2026, with hybrid arrangements most common among mid-size professional services firms in the Loop. Cloud-based accounting proficiency strengthens a candidate's case for remote consideration.
How can I get a bookkeeper job in Chicago with little or no experience?
The most realistic entry path in Chicago is targeting accounts payable or accounts receivable clerk roles at mid-size companies in the West Loop or Fulton Market, where back-office teams frequently promote from within. Chicago's large hospitality and property management sectors also hire bookkeeping assistants with only a high school diploma and basic spreadsheet skills. Completing an associate-level accounting program through City Colleges of Chicago and getting hands-on practice with QuickBooks makes a candidate noticeably more competitive for these openings.
Which industries hire the most bookkeepers in Chicago?
The sectors hiring the most bookkeepers in Chicago are Technology & Software, Government & Public Sector, and Banking & Financial Services, based on current listings on Migrate Mate as of September 2026. Chicago's density of regional headquarters, commercial real estate portfolios, and large nonprofit organizations creates consistent back-office accounting demand across all of those sectors year-round.
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