Top Tech Jobs & Startup Jobs in Chicago, IL

Leads Commercial Surety underwriting strategy, portfolio performance, risk assessment, and technical excellence. Develops and executes underwriting initiatives, monitors trends, ensures compliance, collaborates with Product, Risk, Actuarial, Legal, and Claims teams, and mentors underwriters. The role requires significant large-account Commercial Surety underwriting experience, strategic leadership, strong analytical judgment, and the ability to influence cross-functional stakeholders while supporting profitable growth and underwriting quality.

Senior Underwriting Specialist responsible for underwriting new and renewal professional liability accounts for asset managers, RIAs, private fund managers, and investment firms. Manages a complex portfolio, evaluates risk and pricing, drives profitable growth, develops agency and broker relationships, executes territory plans, identifies cross-sell opportunities, and presents solutions to agents and customers. The role requires regular travel, advanced underwriting expertise, strong financial analysis, negotiation, communication, and informal leadership skills.

Manages complex, high-severity commercial general liability claims, including litigated matters across multiple jurisdictions. Responsibilities include investigating claims, analyzing coverage, interpreting indemnity agreements, setting reserves, directing defense counsel, negotiating settlements, pursuing subrogation and risk transfer, maintaining compliant files, and mentoring claims professionals.

Underwrites and manages a commercial surety portfolio, evaluating financial statements, risks, bond obligations, pricing, and loss factors. The role develops agency, broker, and client relationships; identifies new and renewal business; negotiates complex risks; communicates underwriting decisions; monitors portfolio performance; and supports market development and cross-selling throughout the Midwest.

Lead the development, maintenance, and regulatory compliance of Management Liability and Professional and Executive Lines insurance products, including D&O, EPL, Fiduciary Liability, Cyber, Crime, and Kidnap & Ransom. Draft coverage forms, analyze regulatory and judicial environments, conduct market research, develop filing strategies, respond to insurance department inquiries, support underwriting strategy, and mentor Product Analysts.

Manages complex, high-exposure management liability claims, especially Directors & Officers, Employment Practices, Fiduciary, and Financial Institutions Liability matters. Directs litigation strategy, counsel, investigations, negotiations, settlements, reserves, and coverage decisions. Serves as a claims subject matter expert, mentors adjusters, supports policy development and training, leads process improvements, ensures regulatory compliance, protects data, and collaborates with underwriting, legal, product, and external stakeholders.

Underwrite and manage complex specialty general liability accounts, focusing on high-hazard product liability risks. Identify exposures, evaluate pricing and coverage, make portfolio decisions, and achieve profitability and growth goals. Build agency relationships, solicit and negotiate new and renewal business, present insurance solutions, monitor market trends, and collaborate with claims, loss control, and other business units. Mentor less experienced underwriters and operate with substantial underwriting authority.

Manages complex Employment Practices Liability claims from investigation through negotiation and resolution. Performs coverage analysis, evaluates significant financial exposures, negotiates sensitive settlements, and advises adjusters and leadership. Collaborates with legal, underwriting, agents, vendors, and other stakeholders while ensuring regulatory compliance and accurate documentation. Uses data and analytics to identify trends, mentors less experienced adjusters, and maintains required state adjuster licenses and continuing education.

Conducts on-site property risk engineering assessments for complex and high-hazard industrial accounts. Identifies loss drivers, evaluates fire protection and sprinkler systems, prepares technical reports, recommends risk controls, collaborates with insureds and internal teams, and mentors junior consultants. The role is fully remote for Illinois-based candidates but requires regular regional driving, occasional overnight stays, and infrequent air travel.

Manage complex, high-value insurance claims involving significant legal, financial, and reputational exposure. Lead investigations, coverage and liability analysis, reserving, litigation strategy, negotiations, and claim resolution. Direct defense counsel, collaborate with underwriting, reinsurance, agents, vendors, and legal teams, and serve as a claims subject matter expert. Mentor colleagues, improve workflows and training, provide reporting, support policy and underwriting improvements, and participate in industry education.