Top Tech Jobs & Startup Jobs in Chicago, IL

Contribute to building and hardening micro-apps and AI integrations on a shared GCP platform. Complete bug fixes and small features, participate in code and design reviews, apply security and software development best practices, monitor applications and follow runbooks, and use AI tools to assist development, testing, and documentation while learning from senior engineers.

Lead intake, roadmap, and governance for an AI automation/platform team. Harden and ship business-built AI apps to production with secure GCP platforms, define acceptance criteria and responsible-AI gates, manage vendor buy-vs-build decisions, drive adoption, measure outcomes, and manage AI economics and stakeholder communication.

Build, model, and maintain scalable BigQuery-based data solutions on GCP. Implement performant data models, storage partitioning/clustering, ETL improvements, data validation, and documentation. Collaborate with architects, data scientists, and engineers to deliver governed, high-quality data for reporting and AI initiatives.

Lead strategy and roadmap for AI-powered SaaS features; collaborate with engineering, data science, UX, and GTM teams to define problems, run discovery and experiments, manage backlogs, deliver product outcomes, and drive post-launch adoption and performance improvements.

Lead strategy and delivery of AI-powered, agentic product features for a SaaS insurance platform. Define roadmaps, KPIs, ROI, and success criteria; collaborate with engineering and data science to prototype, test, and launch; drive adoption, mentor junior PMs, and align cross-functional teams from discovery through GTM.

Lead design and governance of enterprise-scale data architecture (warehouses, lakehouses, streaming). Define standards for data quality, lineage, observability, and AI-enabled workflows. Mentor engineers, serve as technical escalation, and translate business needs into long-term data architecture and governance strategies.

Lead portfolio strategy and operating layer for Product and Engineering: build prioritization frameworks, connect roadmaps to financial goals, define reporting/metrics for E-Team and Board, and drive cross-functional initiatives and decision-making.

The Technical Program Manager leads complex technical programs, ensuring cross-functional alignment, managing dependencies, and driving process innovation. Candidates should have extensive experience in program management within technology environments.

Design, build, and operate enterprise-scale multi-cloud infrastructure (Azure primary, GCP, AWS exposure). Own landing zones, Terraform modules, production AKS/GKE Kubernetes, Vault secrets, hybrid networking, CI/CD pipelines, monitoring, DR, and automation (Ansible, Python/Bash). Mentor engineers, document runbooks, and collaborate with security, application teams, and leadership to ensure secure, reliable, cost-optimized cloud platforms.

Lead UX research and design for B2B/SaaS insurance products: create wireframes, mockups, and prototypes; run user research and usability tests; use analytics to measure outcomes; collaborate with product and engineering to implement consistent, validated UX solutions.