Top Tech Jobs & Startup Jobs in Chicago, IL

Build and own cloud-based data pipelines and governed data products supporting Employee Benefits Sales and Underwriting. Design ELT solutions, integrate complex data, improve data quality, and implement CI/CD and enterprise data engineering practices. Architect hybrid cloud solutions using AWS, Hadoop, Spark, Kafka, Snowflake, and related technologies. Influence architecture and tooling decisions, document technical guidance, mentor teams, evaluate emerging technologies, and contribute to strategic roadmaps.

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.

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.

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.

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.

Designs target-state architectures that modernize legacy Employee Benefits platforms and accelerate cloud adoption. Develops end-to-end solutions spanning APIs, microservices, micro-frontends, AI, data, identity, security, and cloud infrastructure. Evaluates technology options, establishes architecture governance, supports roadmaps, and ensures reliability, operability, cost efficiency, and security. Partners with senior leaders, value streams, and engineering teams to deliver cloud-native, AI-ready platforms.

Supports actuarial pricing and product strategy for Small Business commercial insurance. Responsibilities include developing rate indications, refining pricing segmentation, updating loss development factors and assumptions, analyzing deductibles and insurance limits factors, monitoring profitability, and supporting class plan rollouts. The role uses SQL, R, Python, Excel, and related tools to improve analytics, partners with underwriting and product teams, presents results to leadership, and mentors junior actuaries.

Architect and build production-grade agentic AI systems and platforms using Google ADK, MCP, LangChain/LangGraph, and AlloyDB. Develop agent harnesses, RAG/GraphRAG pipelines, vector retrieval and memory stores, Terraform-based GCP infrastructure, CI/CD for model deployments, and enterprise security and governance for sessioned agent interactions.

Lead design and delivery of scalable, secure software across full stack and cloud. Collaborate with product and architecture teams, mentor engineers, drive best practices, integrate AI-assisted tools, and participate in the full SDLC to ensure system stability and performance.