Top Tech Jobs & Startup Jobs in Chicago, IL

Lead end-to-end AI product discovery, prototype and ship working ML/AI solutions for HR, Marketing, and Commercial teams. Build first prototypes yourself, partner with engineers to productionize, define success metrics, and drive adoption and business impact.

Sole designer on a Brand Product squad owning end-to-end product design: user discovery, research, prototyping, and production-ready specs. Partner closely with engineers, contribute to the design system and brand standards, prioritize accessibility, and share craft and AI-augmented workflows across the design org.

Lead and build the DevSecOps function: implement SOC 2 controls, automate compliance and evidence pipelines, own cloud security posture, CI/CD security gates, vulnerability management, and AI-assisted auto-remediation to embed security as code across the developer lifecycle.

Design, build, and maintain scalable, reliable full‑stack systems. Contribute to API and architecture design, write testable code, debug complex issues, improve performance, automate deployments, and mentor junior engineers while collaborating with cross‑functional teams.

Lead a small team (2-4) as a hands-on engineering manager, owning sprint delivery, team health, performance management, and incident response. Contribute to a TypeScript codebase, partner with Product and Design, uphold operational and compliance standards for money-touching products, and champion AI-forward automation, IaC, CI/CD, and observability to ship reliable software.

Design and deliver scalable, secure, and maintainable software systems. Contribute to architecture, build CI/CD pipelines, design distributed systems and APIs, mentor engineers, collaborate with product and design, and improve observability, performance, and operational reliability across teams.

Embed with business teams to discover high-leverage problems and build end-to-end production AI agents, tools, and integrations. Rapidly prototype using agentic coding tools, AI APIs, vector databases, and automation, then deploy reliable, auditable systems that drive measurable business outcomes.

Lead identification, testing, and scaling of new paid channels (streaming TV, programmatic, paid social, YouTube). Design incrementality/holdout tests with BI, own attribution and reporting, build channel playbooks, optimize conversion signal passback, drive creative testing and briefs, manage platform partnerships, and recommend budget/investment decisions to senior stakeholders.

Architect and deliver scalable, secure systems across teams; solve complex cross-team problems; lead large technical initiatives; evaluate emerging technologies; mentor engineers; align technical direction with product and business outcomes while balancing performance, maintainability, and cost.

Own multi-quarter strategy and roadmap for Bankrate's loan-pricing platform components (Loantek, BAP, RMS). Lead cross-functional teams to modernize legacy systems, improve scalability, reliability, and pricing effectiveness, define success metrics, and validate outcomes with customers and advertisers.