Top Tech Jobs & Startup Jobs in Chicago, IL

Lead technical delivery for Life Insurance and Annuity clients: design solutions and architectures, produce technical design docs, mentor distributed teams, drive code quality and integrations (APIs), maintain mainframe and .NET codebases (COBOL, C#, DB2/SQL), and leverage AI tools (GitHub Copilot, Claude Code, custom agents) for automation and efficiency.

Lead data engineering teams to design, build, and maintain scalable cloud-native data pipelines, data platforms, and data products using Snowflake, Databricks, Airflow, and modern architectures. Optimize ETL/ELT, SQL, and transformations for analytics, reporting, and AI use cases; ensure data quality, governance, observability, and stakeholder alignment. Produce documentation, runbooks, and present technical solutions to business and technical audiences.

Lead design and operationalization of enterprise data governance for insurance data across cloud and on-premises estates. Define operating models, stewardship, policies, data standards, quality frameworks, metadata/lineage, tooling, and MDM. Partner with business, actuarial, underwriting, claims, compliance, and tech teams to improve data trust, compliance, and reporting.

Design and deploy end-to-end Generative AI systems across the 7-layer stack. Select and fine-tune models, build LLMOps pipelines, implement observability, integrate with cloud platforms and APIs, enforce data protection, and lead stakeholder workshops to translate business needs into scalable, secure AI solutions.

Design and deploy enterprise Generative AI systems across the 7-layer stack: data ingestion, preprocessing, model selection, orchestration, inference, integration, and application. Lead model selection/tuning (commercial and open-source), establish LLMOps and observability, integrate AI with cloud platforms, enforce data protection, manage hallucinations/security, and act as onshore technical lead for client workshops and stakeholder alignment.

Lead analytics and AI initiatives: define strategy, translate business needs into AI/use cases, oversee dashboards and advanced analytics, run ML/LLM pilots, operationalize models, ensure responsible AI governance, and manage and mentor analytics teams while driving stakeholder alignment.

Remote part-time coordinator schedules appraisal appointments, contacts policyholders via phone/SMS/email, assists homeowners with a mobile photo-capture self-survey app, updates work order statuses, meets productivity and quality goals, troubleshoots technical issues, and communicates issues to management and underwriters.

Senior sales presales leader for Payment Integrity who architects solution strategies, leads executive client engagements, drives presales lifecycle and pricing, crafts value propositions, expands wallet share, and improves win rates through consultative storytelling and cross-functional deal design.

Prepare and track outgoing audit letters, operate and maintain postage and mailroom equipment (inserter, scanner, printers), troubleshoot jams, perform quality checks, monitor supplies, process return mail, report equipment or workflow issues, comply with HIPAA and postal regulations, and meet productivity and quality standards to support audit processes.