Top AI Automation Jobs in Chicago, IL

Design and build automation frameworks and evaluation pipelines for agentic AI products. Develop non-deterministic tests, golden datasets, tool-use validation, prompt regression tests, latency/token monitoring, hallucination detection, and collaborate with AI engineers to convert requirements into measurable automated test cases.

Lead QA Automation for agentic AI products by designing eval pipelines, golden datasets, and automated tests for tool-use, hallucination detection, latency/token monitoring, and regression across models and prompts. Integrate performance testing into CI/CD and collaborate with AI engineers to convert requirements into measurable automated evaluations.

Hands-on intern building automations (Zapier/Power Automate/Make), GPT-based internal assistants, and a light RAG knowledge search. Deliver 3–5 live tools, clean documentation/SOPs, before/after time-saved metrics, and an end-of-summer demo. Onsite in Addison, IL for 10–12 weeks.

The AI Engineer will develop scalable AI systems, automate workflows, and collaborate with business teams to enhance operational efficiency across OpenSesame.

Lead execution of Product Engineering AI and automation initiatives across photonics products. Build and deploy reusable AI/automation tools, transform engineering data into AI-ready systems, and drive cross-functional adoption to improve development, qualification, manufacturing, and reliability processes.

The AI Automation Engineer will apply AI in finance operations to automate processes like AP, AR, and reconciliation, ensuring compliance and performance measurement.

The Director of AI Automation leads AI-driven automation systems, translating strategic goals into practical solutions, managing teams, and enhancing operational efficiency.

Join a talent pool to teach, author, or advise on AI-powered automation. Deliver live workshops, create course materials, design exercises, shape curriculum, review technical content, and support program updates. Part-time (10–15 hrs/week), remote with collaboration in European time zones. Roles span junior to senior levels and emphasize hands-on experience with automation platforms and real-world operational workflows.

The AI Automation Engineer develops AI-driven systems to automate sales and marketing workflows, partnering with various teams to enhance revenue generation and process efficiency.

Develop and maintain an AI-driven pipeline to auto-generate, process, and publish real-life and digital quests. Integrate AI frameworks, design scalable automation workflows, analyze user data to improve generation quality, build API integrations, participate in architecture and documentation, test with pytest/unittest, and collaborate with cross-functional teams to validate LLM outputs against real-world data.