Top Tech Jobs & Startup Jobs in Chicago, IL

Perform reserve studies for specialty financial lines (D&O, E&O, Cyber, EPL, Fidelity), monitor portfolio performance, develop reserving diagnostics and tools, partner with Claims and Pricing to evaluate reserve adequacy, analyze emerging claim trends and significant losses, and drive improvements in data quality, monitoring, and actuarial processes while translating analyses into actionable business insights.

Perform actuarial pricing and reserving tasks for Financial Lines, including rate development, price monitoring, loss ratio planning, profitability studies, reserve analyses, and rate filing support. Partner with Underwriting, Finance, Claims, and IT to improve pricing methodologies, build monitoring tools, analyze trends, and present recommendations to business partners.

Lead a small actuarial team supporting Middle & Large Property lines, owning loss ratio planning, catastrophe risk budgeting, monitoring loss and premium trends, supporting reinsurance, producing pricing and financial materials for leadership, and delivering ad hoc and emerging-risk analyses to improve portfolio performance.

Design and build production-scale data pipelines, orchestration, and integrations on GCP to enable metadata-driven governance, lineage, automation, and AI-enabled workflows. Implement secure, observable, cost-efficient cloud data solutions, embed governance into engineering workflows, and drive CI/CD, testing, monitoring, and platform engineering best practices.

Design, build, and operationalize production-grade AI/Machine Learning solutions and MLOps services. Deploy models and API services to AWS and GCP using CI/CD and IaC, implement workflow automation, monitor post-production performance, research generative/ML techniques, and mentor junior engineers while collaborating with cross-functional data, cloud, and architecture teams.

Lead Applied AI strategy and execution across Employee Benefits and Operations, overseeing ML, generative and agentic AI, RAG, and predictive analytics lifecycles. Drive governance, model risk management, evaluation, deployment, cross-LOB prioritization, talent architecture, and regulatory readiness to improve enrollment, billing, service, and operational efficiency.

Lead planning, forecasting, and performance analysis for P&C lines; partner with finance, actuarial, and business leaders to provide insights, govern models, automate processes, and prepare executive reporting. Drive assumptions for loss ratios, catastrophes, reinsurance analyses, and earnings prep while mentoring a team and implementing analytics and AI-enabled improvements.

Lead employee benefits enrollment strategies and communication campaigns for assigned customers. Manage planning and execution across the enrollment lifecycle, partnering with customers, sales, implementation teams, marketing, operations, and technology vendors. Oversee timelines, deliverables, customer communications, educational content, and engagement initiatives while supporting implementations, presentations, business growth, and continuous improvement. Analyze enrollment performance and build trusted customer relationships to improve participation, product adoption, and customer outcomes.

Manages national employee benefits client accounts from implementation through renewal, serving as the primary customer and broker relationship leader. Responsibilities include issue resolution, service delivery, enrollment and implementation support, renewal coordination, finalist presentations, account growth, plan administration, underwriting communication, eligibility-feed coordination, and process improvement. Requires approximately 20% travel and collaboration with account executives, underwriters, brokers, and internal teams.

Manage regional and national employee benefits accounts from implementation through renewal. Serve as the primary liaison for clients, brokers, underwriters, account executives, and internal teams. Responsibilities include resolving service issues, coordinating enrollment and implementation, leading account reviews and renewals, supporting retention and growth, identifying cross-sell opportunities, presenting tailored solutions, maintaining documentation, and improving customer processes. The role requires employee benefits expertise, relationship management, licensing, a disability specialist designation, and approximately 20% travel.