Top Tech Jobs & Startup Jobs in Chicago, IL

Lead OS modernization, configuration-management migrations, and infrastructure hardening for large-scale Linux environments. Build RPMs, automate runbooks, harden CI/CD and observability, onboard services to monitoring/logging stacks, provide Tier-2 production support and incident response, and document migration and operational procedures.

Lead technical ownership of a globally deployed edge infrastructure for consent and privacy compliance. Design and harden high-performance proxy/CDN components, drive compliance rollouts with risk-mitigation (bucketed rollouts), build platform-agnostic automated tests and CI/CD quality gates, run CDN/WASM proofs-of-concept, mentor teams, and translate technical and legal requirements into reliable production systems.

Design user-centered conversational experiences (voice and chat) using Figma and conversational AI tools. Create journey maps, flows, dialogs, prototypes, and interaction specs; facilitate workshops; collaborate with product and engineering; support testing, tuning, and persona/voice guidelines; mentor junior designers.

Lead application and platform modernization by deconstructing monoliths into container-based services on GCP. Drive Python and PHP development, implement OpenSSL secure communications, expand metrics and logging (Chronosphere/Prometheus/Grafana, Splunk), manage OS/package migrations, ensure testing discipline, mentor engineers, and collaborate cross-functionally to deliver features and troubleshoot distributed systems.

Design, implement, and operate hybrid on-premise-to-cloud network architectures with emphasis on Google Cloud networking (VPC, VPN, Interconnect, LB, firewall). Build and refactor Terraform modules (JSON-driven hydration), troubleshoot routing/DNS/load balancing, automate infrastructure delivery, monitor performance, and ensure reliable, secure network segmentation.

Senior, customer-facing escalation engineer for Google Workspace who diagnoses and resolves complex issues, mentors teammates, improves support processes, documents technical assets, and participates in rotational on-call shifts within a 24x7 global support environment.

Analyze mobile and web user journeys to identify friction, feature adoption, and performance issues. Build custom SQL analyses, create dashboards and visualizations, monitor telemetry to detect problems, and translate insights into executive-ready recommendations that influence product roadmaps and improve user experience.

Build, manage, and optimize production GCP infrastructure (Compute, VPC, IAM, storage, GKE). Execute cloud migrations, implement Terraform IaC, troubleshoot performance and costs, automate with CI/CD and scripts, and collaborate with engineering and client stakeholders to deliver scalable, secure cloud environments.