Senior Accountant – Insurance (Statutory & GAAP)

Hybrid (3 days in office) – Chicago

Oliver James is partnering with a regionally recognized P&C carrier to hire a Senior Accountant to join its core controllership team as the business continues to grow and evolve. This role is ideal for a hands on go getter who wants meaningful responsibility, exposure beyond pure accounting, and the opportunity to grow alongside the business.

This position reports into the Director of Financial Reporting and works closely with the Controller and CFO. You will be a hands-on contributor across statutory, GAAP, and broader finance initiatives – not siloed into narrow tasks.

What You’ll Be Doing

As a core member of the controllership team, you will:

Support monthly, quarterly, and annual close processes
Prepare and review components of statutory and GAAP financial reporting, including schedules and footnotes
Perform account reconciliations, journal entries, and expense allocations
Assist with management reporting, analytics, and ad hoc finance projects
Partner with the team to improve processes, documentation, and controls
Get exposure to broader finance topics, including FP&A and strategic analysis, over time

Profiles That Fits Best

This role will resonate most with candidates who:

Have 3+ years of insurance accounting and/or audit experience with insurance carrier exposure
Enjoy hands-on work rather than rigid, highly segmented environments
Are intellectually curious and want exposure beyond traditional accounting

Backgrounds that tend to do well here include:

Insurance carriers, agencies, or MGAs
Big 4 candidates/regional accounting firms only if candidates have meaningful insurance experience

This is not a fit for someone looking to be trained from scratch on insurance or for a purely review-level role.

Systems & Environment

Oracle ERP
Modern and improving finance technology stack, including emerging AI tools

Location & Work Model

Chicago, hybrid model: 3 days per week in-office

Compensation

Base salary: $100,000 – $120,000
Annual bonus typically 10-15% (not guaranteed)
Competitive benefits package including 401(k), medical, paid parental leave, and PTO

Apply Now

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