Top Finance Jobs in Chicago, IL

Underwrite and bind medium-to-complex workers' compensation risks, follow underwriting guidelines, support payroll partner relationships, issue certificates, assist sales with technical questions, manage high transaction volume, maintain coverage and rating knowledge, and participate in portfolio review. Travel up to 10%.

Lead Pie's Field Underwriting organization owning P&L, portfolio loss outcomes, and the blended onshore/offshore + AI-enabled underwriting operating model. Build and develop teams, set underwriting strategy and standards, partner with Corporate Underwriting, Data Science, reinsurers, and agency partners, and drive adoption of automation while representing the function at the executive level.

Support monthly close and accounting operations under U.S. GAAP: prepare journal entries, reconciliations, variance analyses, and financial statements. Improve processes, internal controls, and automation efforts (including AI tools), partner with finance teams, and assist on ad hoc accounting projects.

Lead corporate actuarial functions for workers' compensation and other P&C lines, managing a team to perform reserving, pricing, ratemaking, predictive modeling, reinsurance optimization, and analytics. Partner cross-functionally, produce financial forecasts and board-level reporting, build reproducible models and data pipelines, and mentor staff while shaping actuarial processes and enterprise risk management.