Top AI Automation Jobs in Chicago, IL

Lead design and delivery of enterprise AI and automation solutions: architect LLM-powered applications, integrate systems and data pipelines, prototype and ship production-grade features, set standards, and lead a small distributed engineering team while translating business needs into measurable automation outcomes.

Lead AI-driven reconciliation and automation to improve encounter data quality. Own model performance, identify root causes, partner with technical and business teams to enhance models, prioritize roadmap, and scale automation while communicating results to stakeholders.

Lead design and execution of test strategies for generative AI systems (LLMs, RAG, agents). Validate accuracy, factuality, fairness, bias, consistency, and security of AI outputs. Create API and model-endpoint tests, automate test suites, perform adversarial and exploratory testing, detect hallucinations, validate data quality and performance metrics, and collaborate with cross-functional Agile/DevOps teams to ensure safe, reliable GenAI deployments.

Lead evaluation, governance, and scaling of applied AI and workflow automation across the enterprise. Partner with business and technical teams to prioritize opportunities, support business cases, drive adoption and literacy initiatives, develop communications, track roadmap and outcomes, and support responsible AI, privacy, security, and compliance alignment.

The role involves designing and implementing automation systems, improving workflows, and developing tools for sales support using AI and automation platforms.

As a Staff AI Engineer, you will design and implement AI-powered automation for internal departments, manage the full project lifecycle, and enhance various processes across CargoSprint, focusing on business impact and collaboration.

Design and build AI- and automation-driven solutions to accelerate Mortgage Cadence Platform configuration using LLMs and workflow automation. Develop integrations with system APIs, partner with implementation teams, create documentation and training, and propose new tools to improve implementation accuracy and scale.

Design and deliver AI-powered analytics, dashboards, and decision-support tools for commercial healthcare teams. Build LLM-based agents, use cloud data platforms (Azure/AWS/Snowflake), ensure data governance and compliance, translate complex healthcare data into executive-ready insights, and automate insight generation to support growth and operations.

Develop and manage intelligent automation solutions using UiPath, bridging communication between project managers and clients, conducting process analysis, and providing documentation.

Design and execute test strategies and automation for cloud-native and GenAI/AI-ML systems. Perform functional, integration, performance, security, and API testing; validate model accuracy, fairness, robustness, and data quality; integrate automation into CI/CD; track defects; mentor junior QA engineers.

The AI Automation Engineer will automate internal processes, mentor non-technical staff on building tools, and ensure solutions deliver measurable business impact using AI technologies.

Lead enterprise adoption of Microsoft Copilot, Copilot Studio, and Power Platform by analyzing business processes, designing AI agents, building ROI-backed automation roadmaps, delivering training and prompt engineering best practices, and measuring utilization and productivity improvements across functions.

Client-facing Associate leads workstreams for process improvement, intelligent automation, and AI-enabled transformation. Responsibilities include process discovery, facilitating workshops, analyzing processes and data, designing future-state processes and implementation roadmaps, preparing executive deliverables, partnering with technical teams to design and deploy automation, and supporting change management. Mentors Analysts and contributes to proposals, methodologies, and thought leadership. Requires strong collaboration and consulting skills, frequent travel, and 2+ years relevant experience.

Lead development and execution of MVB's AI and automation strategy, including Generative and Agentic AI and RPA. Partner with business and technical stakeholders to design, pilot, and scale solutions, establish governance and best practices, monitor performance metrics, manage vendors, and deliver training to ensure ethical, secure, and effective AI deployments.

Build AI-powered workflows, agents, and integrations to automate marketing research, creative asset preparation, campaign analysis, reporting, and internal coordination. Prototype and productionize LLM-based tools, connect data sources and ad platforms, validate automation quality with real use cases, and document systems for reuse and scaling.

Build and maintain internal and customer-facing web/cloud apps and AI automations. Integrate with third-party APIs (QuickBooks, Microsoft Graph, Zoho, Zoom), implement generative-AI features, ensure security, deploy to cloud, and collaborate with leadership and IT. Work independently on design, testing, and maintenance across varied projects.

Build and ship AI-driven automation across the go-to-market lifecycle: prospecting, lead routing, deal support, retention, and instrumentation. Design agents and workflows, connect GTM systems and data, deploy and monitor production AI, set guardrails and evals, and partner with Sales, Solutions Architecture, Marketing, and RevOps to measure and improve impact.

Lead design and delivery of agentic AI systems and LLMOps on AWS to generate, validate, and deploy infrastructure-as-code (Terraform). Build multi-agent applications, RAG pipelines, and AIOps for cloud operations; integrate AI into CI/CD and ITSM. Set technical direction, establish guardrails/policy-as-code, curate reusable Terraform modules, and mentor engineering teams.

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.

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.

Responsible for building tools and frameworks to scale AI and ML capabilities through automation, enhancing the speed and consistency of analytics delivery.

Build and maintain LLM-powered agents and automation pipelines to create, review, and publish educational content. Integrate and optimize Skilljar and Sanity CMS, eliminate content ops bottlenecks, partner cross-functionally, and implement interactive learning components to scale personalized learning.

Design and build AI-powered automation workflows and integrations for Pragmatico and clients. Lead discovery, architect solutions using LLM APIs and integration platforms (Zapier/Make.com), present solutions to stakeholders, train client teams, and create reusable automation frameworks and thought leadership content.

Designs, builds, tests, and deploys AI-enabled automations and copilots for GTM and RevOps. Creates reusable agent templates, prompt libraries, and orchestration patterns; implements end-to-end API integrations; monitors performance; documents and hands off production solutions; and trains/coaches business teams on safe, responsible AI usage and prompting best practices.

Design, build, and scale AI-powered automation using LLMs, RAG, vector DBs, prompt pipelines, and agent systems. Integrate with internal tools and cloud platforms, implement orchestration, observability, security guardrails, measure impact, and partner cross-functionally to replace manual processes with reliable production-grade automation.