Top Tech Jobs & Startup Jobs in Chicago, IL

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.

Leads the global benefits strategy covering health, wellness, retirement, governance, compliance, vendor management, financial stewardship, and employee experience. Oversees benefits innovation, AI and technology adoption, analytics, dashboards, fiduciary responsibilities, regulatory reporting, and merger-related benefits integration. Advises senior leadership, manages multimillion-dollar budgets, leads a high-performing team, and drives benefits transformation across a large, complex organization.

Executes DAIO workforce strategy through workforce planning, demand and skills analysis, data-driven recommendations, transformation workstream management, change impact assessment, stakeholder engagement, and adoption planning. Partners with HR, technology, learning, and DAIO leaders on skills forecasting, upskilling, build-versus-buy analysis, governance, and executive decision support.

Designs, builds, operates, and automates SQL Server database infrastructure across Windows, VMware, and AWS EC2. Partners with database specialists to enhance AWS database products, implement fault-tolerant and observable systems, manage configuration and deployments, troubleshoot performance, and improve operational effectiveness using automation and AI tools. The role also supports backup and recovery, security, monitoring, auditing, licensing, and infrastructure reliability.

Data Engineer Interns support data pipelines, workflows, and platforms that enable analytics, reporting, automation, machine learning, and AI initiatives. Responsibilities include ingesting and transforming structured and unstructured data, applying data quality and validation practices, collaborating on scalable data solutions, and using Python, SQL, ETL processes, cloud technologies, and AI tools. The role includes mentorship, Agile exposure, and hands-on experience supporting data assets for insurance business needs.

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.

Lead infrastructure resilience for cloud and SaaS systems by implementing observability, IaC, CI/CD automation, incident triage and self-healing. Build tooling, alerts, AI-driven anomaly detection and runbooks, partner with architecture and infrastructure teams to improve reliability, performance, and security.

Lead development and maintenance of workers' compensation pricing methodologies and tools. Update model parameters, drive pricing initiatives, collaborate with underwriting/product/data science/IT, provide profitability analyses, and support implementation to improve accuracy, segmentation, and profitable growth across business segments.