Top Tech Jobs & Startup Jobs in Chicago, IL

Handles complex contract and commercial surety claims across multiple jurisdictions, including investigation, negotiation, resolution, salvage, and subrogation. Advises on legal and transactional matters, prepares surety agreements, manages outside counsel and consultants, and supports underwriting teams through training and legal guidance. Drives process improvements, organizational change, and strategic claim outcomes while maintaining knowledge of applicable laws and regulations.

Handles litigated and non-litigated commercial general liability claims nationwide. Responsibilities include evaluating coverage and risk transfer, ensuring accurate reserves, investigating claims, selecting experts and counsel, negotiating resolutions, developing claim strategies, and communicating with internal and external stakeholders. The role requires extensive bodily injury and commercial general liability claims experience, contractual analysis skills, adjuster licensing, and strong legal, negotiation, communication, and computer skills.

Conduct virtual audits of workers’ compensation and general liability policies by analyzing financial records, verifying exposure classifications, calculating earned premiums, resolving rating discrepancies, and ensuring regulatory compliance. Communicate findings with policyholders, producers, underwriters, and internal teams; provide account support and customer service. The role includes structured training, independent audit management, and ongoing research into industry rules and regulations.

Leads internal consulting efforts focused on AI, automation, and operations transformation. Defines future-state operating models, evaluates and prioritizes initiatives, redesigns workflows, develops implementation roadmaps, and establishes KPI and benefits-realization frameworks. Partners with business, operations, product, IT, data, and executive stakeholders to improve deployment readiness, manage risks and dependencies, translate business needs into requirements, and track measurable value from transformation initiatives.

Leads sales and distribution strategy across AmTrust’s Northeast region, overseeing regional sales managers, agency and broker relationships, market expansion, and profitable growth. Partners with underwriting and executive leadership, develops talent, analyzes market and sales data, strengthens distribution channels, and represents the organization in executive and industry engagements. The role requires extensive travel throughout the Northeast and residence within the region.

Directs a major loss workers’ compensation claims unit and supervises 4–8 complex-claims adjusters across multiple locations. Leads hiring, training, mentoring, performance management, quality assurance, compliance, reporting, process improvement, and succession planning. Provides oversight on complex claims, ensures adherence to jurisdictional regulations and company policies, and presents performance information to senior leadership. Preferred experience includes Pennsylvania and New Jersey workers’ compensation claims.

Develop and maintain C# business rules within rules-engine applications, translating stakeholder requirements into scalable and maintainable code. Optimize and troubleshoot rule execution, integrate databases, APIs, and external systems, and participate in testing, code reviews, and documentation. Partner with Product, Sales, Underwriting, and Actuarial teams to support commercial insurance growth and profitability strategies through business analysis, recommendations, and industry-focused product solutions.