Top AI Automation Jobs in Chicago, IL

Lead end-to-end delivery of custom technology solutions across supply chain functions (planning, manufacturing, warehouse, logistics, merchandising). Define architectures and roadmaps, identify agentic AI use cases, guide development/testing/deployment, lead cross-functional teams, manage scope/timelines/budgets, and run client workshops to translate technical solutions into business outcomes.

Lead AI partnership strategy and execution to grow AI Frontier Labs alliances. Own alliance performance, co-sell pipeline, joint GTM and solution development, partner account mapping, enablement, marketing, and executive alignment to scale generative AI adoption and revenue.

Design and analyze rigorous messaging experiments using A/B testing and causal inference. Build measurement frameworks, data pipelines, dashboards, automated analyses, and scalable data solutions for messaging campaigns. Partner with CRM, Product, Algorithms, and Engineering teams to translate ambiguous business questions into actionable recommendations and experimentation standards. Support messaging strategy across channels, timing, content, targeting, and new business verticals.

Lead client engagements in insurance data, analytics, and AI: define roadmaps, run discovery sessions, design solutions, manage delivery and teams, develop proposals, and ensure DataOps, cloud (AWS), governance, and best practices across AI and analytics initiatives.

Build AI-powered workflows, agents, integrations, and internal tools that automate People Operations. Partner with People, Engineering, and IT to modernize onboarding and other employee processes, while implementing secure access controls, human oversight, escalation paths, and production-ready architectures. Prototype with users, iterate quickly, and measure improvements in efficiency, employee experience, and operational consistency.

Leads AI presales strategy, customer advisory, technical solution architecture, and team development. Translates business needs into AI use cases, prototypes, business cases, roadmaps, and repeatable offerings. Partners with sales, engineering, consultants, and technology vendors to support complex pursuits, executive briefings, demonstrations, proofs of concept, and AI business growth. Promotes responsible AI governance, tracks pipeline performance, develops thought leadership, and remains hands-on in high-impact customer engagements.

Identifies business opportunities for AI and automation, gathers and documents requirements, develops business cases, supports solution design and delivery, facilitates stakeholder collaboration, assists with testing and change management, and tracks project outcomes, reporting, and benefits realization.

Lead end-to-end design of AI-enabled networking experiences: convert ambiguous AI opportunities into product concepts, prototypes, and shipped features. Define AI-first interactions, data and telemetry requirements, reusable UX patterns for control and explainability, and partner with platform, engineering, and research teams to deliver trustworthy, measurable intelligence features.

The AI Deployment Engineer will build, deploy, and scale AI solutions while collaborating across departments to ensure successful implementation and support of operational workflows.

Leads company-wide AI adoption, operating the AI Center of Excellence, developing champions, running cross-functional AI sprints, delivering training, managing AI tools and budgets, and measuring workflow adoption, time savings, and financial impact. The role partners with Engineering to distribute shared AI skills, evaluates vendors, reports outcomes to executives, and publishes successful use cases across departments.

Lead the architecture and development of Jerry.ai’s next-generation AI and automation platform. Own conversational agents, voicebots, computer-use agents, backend workflow automation, document validation, transaction orchestration, and external insurance-system integrations. Evaluate emerging AI technologies, deploy production LLM systems, and partner with OpenAI on advanced voice and workflow solutions. The role requires end-to-end software ownership, strong architectural judgment, and experience managing evaluations, regressions, latency, cost, and failure handling.

Architect and build production agentic AI systems for customer support and compliance automation. Lead technical direction for distributed systems, APIs, orchestration frameworks, guardrails, and evaluation systems. Create reusable automation primitives, improve grounding and reliability, reduce hallucinations, and mentor engineers on LLM application design and production readiness. Collaborate cross-functionally to scale AI automation across Coinbase.

Own the strategy, architecture, evaluation, and production deployment of Jerry.ai’s next-generation AI agents and workflow automation platform. Lead conversational agents, voicebots, computer-use agents, document validation, transaction orchestration, and external insurance-system integrations. Evaluate emerging AI technologies, make technical investment decisions, partner with engineering and OpenAI, and ensure systems meet requirements for reliability, latency, cost, regression prevention, and failure handling.

Build and scale agentic AI systems that automate customer experience workflows across Slack and Salesforce. Analyze transcripts, detect SLA risks and escalations, provide self-service operational insights, and develop AI memory architecture. Partner with data, QA, workforce management, and customer advocacy teams to ensure system accuracy, reliability, trustworthy outputs, and measurable operational impact. Productize internal tools and design human escalation patterns for scalable deployment.

Build and operate an AI-driven global sourcing platform covering web crawling, data ingestion, normalization, entity resolution, product matching, provenance, and source monitoring. Integrate Zoho CRM and QuickBooks, apply LLMs with structured evaluation and human review, and identify automation opportunities across business departments. Lead pilots, train employees, measure impact, and scale the platform to hundreds of sources.

Leads enterprise AI transformation by developing the AI roadmap, prioritizing investments, managing initiative portfolios, and delivering measurable business value. Partners with executives and cross-functional teams to redesign operations, establish governance, evaluate technologies and vendors, drive adoption, and lead workforce change. Accountabilities include revenue growth, productivity, efficiency, customer experience, compliance, AI maturity, and value realization.

Build two AI-assisted reporting systems that consolidate account and internal data, validate KPIs, automate refreshes and recurring report delivery, generate AI summaries, and produce dashboards. The contractor will independently manage requirements, integrations, error handling, documentation, cost assumptions, timeline, and execution under a fixed-scope project engagement.

Hands-on technical leader who designs, builds, and deploys production-grade AI automation and agentic workflows. Responsibilities include rapid prototyping, RAG and document-intelligence systems, API integrations, orchestration, monitoring, reusable AI assets, and mentoring a small engineering team to deliver frequent releases and measurable business impact.

Design and author practical courses on AI and workflow automation adoption. Develop curricula, case studies, templates, exercises, and frameworks; translate implementation experience into actionable learning content; review technical accuracy; facilitate sessions; and teach responsible AI controls, workflow redesign, scaling, and value measurement.

Build and deploy AI-enabled automation solutions across enterprise systems. Partner with Business Applications, Data & Analytics, and IT teams to analyze processes, identify automation opportunities, integrate platforms, test and monitor solutions, document implementations, and train process owners. The role requires hands-on coding, AI workflow experience, enterprise integrations, scripting, SQL, structured data knowledge, production support, and strong communication with technical and non-technical stakeholders.

Develops AI and automation solutions for Commercial Operations by partnering with business stakeholders and IT. Responsibilities include designing agentic AI capabilities, integrating AI with enterprise data platforms and workflows, enabling data-driven decisions, evaluating emerging technologies, and scaling successful use cases. The role requires strong application or data experience, commercial operations knowledge, programming skills, cloud-native data services experience, and hands-on LLM agentic AI expertise.

Build and deploy production micro-apps and LLM-powered agents on a governed GCP platform. Integrate AI with systems (Salesforce, Slack, NetSuite, SQL), harden apps with auth, secrets, CI/CD, logging and monitoring, automate maintenance, and implement evaluation and observability for model quality and drift.

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

Build and deploy AI applications, agents, intelligent workflows, document-processing solutions, predictive analytics, and automation. The role spans AI use-case assessment, solution design, prototyping, evaluation, testing, production deployment, monitoring, governance, and responsible-AI controls. The engineer will integrate AI with enterprise systems, APIs, workflows, and data platforms while partnering with engineering, cybersecurity, governance, and mission teams in a federal environment.

Design and deliver LLM-powered, agentic AI systems to automate customer support and compliance. Build scalable, secure backend infrastructure in Python and Go, integrate third-party models/APIs, implement grounding and guardrails, and measure performance. Lead end-to-end projects, mentor engineers, conduct code reviews, and participate in on-call and incident response to improve resolution times and reduce operational costs.