Top AI Automation Jobs in Chicago, IL

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.

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.