Top Tech Jobs & Startup Jobs in Chicago, IL

This role involves owning the security architecture for AI platforms on GCP, designing guardrails, and integrating security into CI/CD pipelines. Candidates should have extensive experience in cloud security, specifically with GCP services, Kubernetes security, and AI/ML security practices.

Load, validate, normalize, reconcile, and report client investment data using Excel, SQL, VBA, and Python. Work with development teams to automate and improve onboarding, apply accounting and securities knowledge, lead improvements, and coordinate complex activities within an agile environment.

Work as an independent contractor showing homes, hosting open houses, and attending inspections on a flexible schedule. Earn flat-rate pay per field event. Requires a state real estate license, affiliation with Redfin, local MLS/Realtor association membership, smartphone/laptop/GPS, and reliable transportation. No contract closings required; optional training provided.

Lead regulatory strategy and compliance for Mastercard's global money transmission/payment licenses. Advise product and operations teams, manage regulatory examinations and external counsel, design compliance controls, monitor regulatory changes, engage with regulators, and report to senior management.

Lead and mentor an SRE team to drive reliability, automation, and performance for cloud-based systems. Embed with engineering teams to improve production excellence, participate in on-call incident response, debug cross-stack issues, and deliver system design and operational improvements.

Design, build, and maintain scalable test automation frameworks and CI/CD-integrated pipelines. Lead functional, integration, regression, and performance testing across distributed systems and telephony platforms. Mentor engineers, analyze failures using logs/metrics, execute load/stress tests, and improve test infrastructure, reliability, and engineering productivity.

Select the world’s best golf-playing practicing lawyer to attend the Legora Invitational in NYC on Sept 2, 2026. Play golf with leading lawyers and Ludvig Åberg, present a written, specific case about how you use Legora, demonstrate putting ability, and join discussions about the future of law and legal technology. Travel and accommodation covered.

Support firm-wide compliance by managing employee registration and licensing (FINRA/NFA), administering compliance databases, tracking attestations and projects, coordinating regulatory training, assisting with internal/external exams, and working with business teams to resolve compliance matters. Role is hybrid Chicago-based and designed for growth into broader compliance responsibilities.

Lead SRE efforts for DFIN SaaS: ensure availability, performance, scalability, and automation. Implement monitoring, CI/CD, IaC, container orchestration, AI-enhanced observability, incident response, RCA, and runbook automation while collaborating across engineering teams.

Lead QA efforts by designing and executing test strategies, creating automated and manual tests, tracking defects, maintaining traceability matrices, reporting findings, and collaborating with cross-functional teams to ensure product reliability and continuous improvement.