Top Tech Jobs & Startup 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.

The Senior Manager, Underwriting leads the New Business Underwriting team, ensuring performance, service delivery, and development of underwriters while driving process improvements and managing team dynamics.

Manage workers' compensation claims end-to-end: investigate, determine compensability, set reserves, administer benefits, control litigation, negotiate settlements, and provide claim status and guidance to agents and insureds while ensuring statutory compliance and excellent customer service.

The Claims Adjuster manages workers' compensation claims end-to-end, ensuring legal compliance, mitigating exposure, and providing excellent customer service to agents and clients.

Lead and scale Pie's claims adjudication function for workers' compensation across jurisdictions. Own strategy execution, team structure, KPIs, budgets, large-loss settlements, regulatory compliance, and claims technology adoption. Partner with Claims, Underwriting, Actuarial, Product, Finance, Legal and external stakeholders to drive improved claims outcomes, loss ratios, and customer experience while building senior talent and governance for adjudication operations.

Manage employee relations, ensure labor law compliance, support performance management, administer benefits and leave, maintain HRIS data and reporting, run workforce analytics for diversity, support onboarding and headcount processes, and improve People systems and programs while partnering with leaders and cross-functional teams.

Lead HRMS implementation, maintenance and support activities: ensure data integrity, troubleshoot issues, design processes, build reports and dashboards, run testing and integrations, and partner with People teams on training and improvements.

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.