Top Tech Jobs & Startup Jobs in Chicago, IL

Leads the technology strategy, modernization, and execution for Employee Benefits and Employer Experience platforms. Oversees cloud-native, API-driven engineering, AI-first development, DevSecOps, application modernization, and enterprise technology roadmaps. Builds high-performing global engineering teams, drives organizational transformation, manages vendors, aligns technology with business priorities, and promotes engineering excellence, responsible AI adoption, productivity, resilience, and continuous improvement.

Provides insurance defense representation for complex general liability matters in Illinois. Responsibilities include legal research, defense strategy development, pleadings, discovery, depositions, motions, briefs, client communication, negotiations, court appearances, hearings, arbitrations, and trials under attorney supervision. The role is remote but requires travel within the assigned jurisdiction for court appearances and occasional in-office meetings.

Leads customer strategy for Middle and Large Business commercial insurance, creating and activating a customer blueprint that drives value, loyalty, retention, growth, resilience, risk prevention, and simpler experiences. Aligns sales, underwriting, claims, risk engineering, operations, service, and innovation leaders around customer outcomes. Develops playbooks, governance, metrics, and operating routines while embedding customer-centricity across business planning and execution.

The Senior Catastrophe Risk Modeling Analyst supports underwriting through catastrophe modeling and exposure management, primarily for Latin America, and collaborates with various teams to improve risk assessment and reporting.

Build and own cloud and hybrid data pipelines and governed data products supporting Sales and Underwriting. Architect, implement, test, and optimize ELT solutions using AWS, Snowflake, Spark, Kafka, and related technologies. Ensure data quality, governance, documentation, CI/CD, and operational standards while influencing architecture and tool decisions. Mentor team members, communicate complex technical concepts, support roadmaps, and evaluate emerging data, analytics, and AI technologies.

Designs and supports AWS cloud infrastructure, Infrastructure as Code, CI/CD pipelines, containerized deployments, monitoring, observability, and DevSecOps capabilities. Troubleshoots environments, improves software delivery and operational reliability, collaborates across engineering and security teams, contributes to cloud architecture, and mentors less-experienced engineers. The role also evaluates AI-assisted tools and emerging technologies to improve productivity, quality, and delivery outcomes.

An 11-week hybrid summer internship developing statistical, machine learning, and AI solutions for insurance business problems. The intern will assess data sources, build and deploy analytical tools, support business strategies, present insights to technical and non-technical stakeholders, document work, and gain experience with cloud environments, modeling techniques, and emerging AI workflows.

Design, build, and modernize Guidewire ClaimCenter solutions, Java APIs, and cloud-native AWS services for claims operations. Own end-to-end delivery, including testing, CI/CD, observability, releases, and production support. Partner with business and operations teams to identify automation opportunities, prototype solutions, and productionize successful capabilities. Lead incident resolution, mentor engineers, develop implementation playbooks, and build Google ADK agents for document understanding, claims decision support, and workflow orchestration.

Build and enhance enterprise AI platform services spanning AIOps, MLOps, FMOps, and LLMOps. Develop GenAI and ML capabilities across Google Cloud, AWS, and Azure; architect scalable solutions; implement monitoring, CI/CD, testing, and serverless applications; and promote engineering best practices. The role also involves collaborating across data science, business, and cloud teams, mentoring engineers, reviewing system designs, and advancing RAG, vector search, agentic frameworks, and responsible AI capabilities.

Leads enterprise Responsible AI governance, overseeing AI and Generative AI risk assessments, fairness testing, model evaluations, monitoring, controls, and lifecycle governance. Advises business, technical, legal, compliance, and risk stakeholders; develops scalable governance frameworks; and evaluates emerging technologies such as foundation models and agentic AI. Drives controls for monitoring, human oversight, intervention, containment, and system shutdown while balancing regulatory obligations, risk management, innovation, and business value.