Top Prompt Engineering Jobs in Chicago, IL

Design, test, deploy, and continuously improve prompts and system instructions for AI agents supporting enrollment, learning, and student success. Build evaluation frameworks, monitor production performance with observability tools, conduct red-team testing, manage prompt versioning, and collaborate with engineers, product managers, learning designers, faculty, and university stakeholders. Translate educational and operational requirements into reliable agent behavior across RAG, multi-turn, voice, and multimodal experiences.

Design, test, and document prompts and prompt libraries to optimize AI language model outputs. Collaborate with product, data, and ML engineers to integrate prompt solutions, run A/B experiments, measure performance, and maintain versioned documentation. Support TIBCO-specific implementation and stay current on AI/NLP techniques.

Lead and establish Five9s AQM Prompt Engineering practice: define methodology and standards, build reusable prompt libraries, mentor a small team, lead complex customer engagements, validate prompts with sampling and precision/recall analysis, collaborate with product and pre-sales, and deliver training and enablement for prompt-driven QM deployments.

Design, author, and iteratively optimize LLM evaluation prompts for Five9 AQM; define evaluation scope and pass/fail criteria with customers; select and analyze call samples; measure precision/recall; maintain a versioned prompt library; collaborate with QA and implementation teams; debug prompt failures; develop standards, templates, and support pre-sales demonstrations.

As an AI Prompt Engineer, you'll develop prompt templates, conduct A/B tests, collaborate with trainers, and maintain prompt libraries for generative AI applications.