Top Tech Jobs & Startup Jobs in Chicago, IL

Provides multi-line loss control and risk management services for specialty insurance programs. Evaluates exposures, conducts risk assessments and audits, ensures state regulatory compliance, supports MGA onboarding, authors safety resources and reports, coordinates with loss control providers, and analyzes portfolio-level loss data. Primarily supports workers’ compensation, property, auto, general liability, and professional liability programs. National travel of approximately 20% is required.

Leads environmental casualty and excess insurance underwriting, overseeing teams, financial performance, broker relationships, product development, reinsurance placement, pricing, and market strategy. Partners with claims, risk management, finance, and actuarial teams to align underwriting practices with organizational goals. Drives process innovation, continuous improvement, and profitable growth while managing strategic wholesale distribution relationships and developing high-performing teams.

Leads regional sales and marketing of commercial insurance products through independent agencies and brokers. Develops territory strategies, drives premium growth, manages agency relationships, follows up on submissions and quotes, trains agents on products and digital systems, monitors market trends, and achieves revenue goals. This outside-sales role requires extensive travel throughout Northern Illinois and other assigned states.

Lead a team of 12–16 Premium Auditors conducting workers’ compensation, general liability, and commercial-line audits. Oversee workforce planning, recruitment, training, workload allocation, production, quality assurance, regulatory compliance, reporting, and performance management. Resolve complex audit issues with insureds, agents, underwriters, and internal stakeholders. Use audit findings and performance data to improve processes, mitigate risk, and maintain compliance with state requirements and company standards.

Handles litigated and non-litigated commercial general liability claims, including exposure recognition, reserving, coverage analysis, risk transfer, investigations, counsel and expert selection, negotiations, and resolution strategies. Provides customer service and communicates with internal and external stakeholders. Periodic travel may be required for mediations, trials, and related meetings.

Leads and mentors a team managing complex, high-severity commercial general liability claims. Oversees investigation, coverage analysis, liability and damages evaluation, reserving, litigation, negotiation, and settlements across multiple jurisdictions. Ensures regulatory and quality standards, reviews claims performance, develops employees, manages staffing and administration, monitors reporting, improves workflows, and stays current on legal and industry developments.

Develop business strategies, operating models, capability analyses, roadmaps, and strategic projects. Partner with leadership, product owners, and delivery teams to define requirements, manage risks, track milestones, implement changes, and deliver business outcomes. The role requires consulting, business analysis, process improvement, project, product management, agile, financial analysis, and change management experience.

Conducts complex virtual and physical premium audits for Workers Compensation and General Liability policies. Reviews financial records, validates exposure classifications, resolves policy issues, and ensures accurate earned premium calculations in accordance with regulations and company procedures. Collaborates with insureds, underwriters, and producers; provides audit guidance, maintains customer service, and mentors junior staff. The role requires strong Excel, analytical, communication, and organizational skills, with occasional physical audit activity possible.

Develops nonprofit insurance business across an assigned region by prospecting and managing agency and broker relationships. Builds market-development strategies, supports regional sales managers, conducts agency visits, provides product expertise and training, monitors submissions and pipelines, and delivers competitive intelligence. The role drives premium growth, agency production, and sales objectives while coordinating with underwriting and other business units. It is a remote, outside-sales position requiring travel.

Supervise actuarial predictive modeling initiatives for insurance pricing, portfolio management, and planning. Collaborate with actuaries, data scientists, underwriters, and management to develop, validate, govern, and implement models. Establish assumptions, loss adjustments, usage guardrails, monitoring practices, and model documentation. Support regulatory filings, improve team workflows, contribute to strategic projects, and mentor staff in actuarial and technical skills.