Top AI Automation Jobs in Chicago, IL

Leads Highmark Health’s Finance AI strategy, roadmap, governance, and transformation. The role identifies and scales AI and automation use cases, redesigns finance processes, establishes controls for responsible AI use, manages vendors and partners, tracks value and risk, and drives adoption through training and change enablement. Responsibilities span accounting, forecasting, reporting, finance operations, data integrity, model oversight, regulatory compliance, and cross-functional collaboration.

Build and maintain production LLM-based agents and automated digital customer success journeys. Analyze customer behavior, design playbooks and agent architectures, write Python integrations, create evaluation and regression tests, deploy and monitor production systems, and continuously improve performance. The role partners cross-functionally to increase product adoption, reduce churn risk, and improve retention and expansion across a high-volume B2B SaaS customer base.

Design and implement AI agents, plugins, automations, and enterprise integrations for HR Technology platforms. Lead requirements gathering, technical analysis, solution design, testing, documentation, deployment, security, and data integrity efforts across HR, IT, and business stakeholders. Integrate platforms including ServiceNow, Workday, and other enterprise applications while supporting the HR automation and AI roadmap.

Build and deploy AI-enabled solutions for Marketplace operations and commercial challenges. Identify opportunities, frame ambiguous business problems, develop prototypes using enterprise data and AI/LLM tools, validate business value, and transition successful solutions into production. Partner with business, product, technology, and data teams; drive adoption, measure outcomes, coordinate initiatives, mentor team members, and enhance reusable platforms and frameworks.

Own the enterprise AI strategy, roadmap, governance, investment priorities, and measurement framework. Identify and prototype high-value AI use cases, guide pilots into production, establish responsible-AI standards for sensitive data, and communicate outcomes to executives. Build adoption through enablement and reusable practices while coordinating technology, business, legal, security, data, and vendor partners. Lead the emerging AI strategy function and hold teams accountable for delivery and value realization.

Leads enterprise AI strategy, product roadmapping, and cross-functional transformation initiatives. Identifies and scales high-impact AI use cases, oversees solution development and deployment, redesigns workflows, drives adoption, advises executive leadership on AI investments and governance, and establishes KPIs for efficiency, cost, quality, and client outcomes. The role also mentors associates and manages stakeholders across business, operations, and technology teams.

Supports enterprise growth through strategic market research, business analytics, account intelligence, and AI innovation. The intern will research companies and competitors, analyze market trends, prepare strategic presentations, and help design and test AI agents and intelligent workflows for automated research and reporting. The role collaborates with Sales and Marketing while identifying ways to improve productivity and decision-making using generative AI and emerging technologies.

Build and maintain AI-powered workflows, agents, automations, internal tools, and production systems for creative ideation, copy generation, video pipelines, reporting, and client delivery. Integrate LLMs and third-party APIs, ship rapidly, iterate based on real usage, and develop practical tools that improve marketing operations.

Design, build, and operate production AI automations and agentic workflows for Toast’s customer care systems. Integrate LLMs with Salesforce Service Cloud, Amazon Connect, and workflow platforms; develop autonomous actions with human oversight; test, monitor, and improve system reliability, accuracy, latency, and cost. Collaborate with software engineers, Salesforce developers, and care operations stakeholders to translate workflows into scalable intelligent solutions.

Leads engineering teams delivering enterprise AI, intelligent automation, digital capture, and document intelligence platforms. Owns technology strategy, architecture, modernization, operational excellence, governance, reliability, security, and compliance for mission-critical systems. Develops engineering organizations through hiring, coaching, succession planning, and performance management while partnering with product, architecture, operations, business, and executive stakeholders. Drives adoption of generative AI, agentic automation, workflow orchestration, cloud-native architecture, and modern delivery practices to achieve measurable business outcomes.

Leads the delivery, integration, adoption, and scaling of AI-powered solutions across the firm. Translates AI strategy into production workflows, automation systems, enterprise integrations, and measurable business outcomes. Oversees technical implementation, vendors, delivery roadmaps, governance, change management, training, and continuous improvement. Partners with technology, data, and business teams to embed AI into workflows and improve productivity, client experience, and operational efficiency.

Build, test, and support AI-powered applications and workflow automations using Microsoft Power Platform, GPTs, agents, APIs, and automation tools. Configure prompts, integrations, and knowledge sources; troubleshoot workflows; conduct testing and UAT; document solutions; support deployments and users; and follow information security practices. The role offers guided development for an early-career engineer with foundational programming, AI, automation, and software skills.

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.

Build and deploy AI-powered automation workflows for marketing, growth, content, sales collateral, social distribution, and community operations. Responsibilities include auditing existing processes, automating blog production and publishing, encoding brand voice, integrating platform APIs, implementing human approval steps, documenting workflows, and handing them off to the team.

Leads forensic automation and cognitive technology engagements, delivering machine learning, data science, predictive modeling, and statistical solutions for enterprise clients. Designs scalable pipelines and reusable analytics components, integrates cloud and enterprise data, presents findings to executive and legal audiences, manages teams, and provides client and internal training.

Own Cerby’s AI agents for API catalog generation, browser workflow creation, and self-healing automation. Take existing systems into production using durable workflows, observability, evaluation benchmarks, cost controls, and security protections. Responsibilities include detecting and repairing automation drift, managing credential isolation and prompt-injection risks, defining threat models, partnering with engineering teams, writing design documentation, mentoring contributors, and providing on-call ownership after launch.

Leads consulting engagements that design, build, evaluate, and deploy enterprise agentic AI and infrastructure automation solutions. Responsibilities include multi-agent orchestration, LLM and model-platform integration, RAG, tool and API connectivity, guardrails, observability, testing, and production rollout. The role advises client executives, translates business needs into AI strategies, mentors engineers, develops reusable architectures and evaluation assets, and drives responsible, measurable AI outcomes.

Leads the architecture and development of enterprise AI and automation solutions, including LLM applications, intelligent workflows, system integrations, and data pipelines. Owns end-to-end delivery, establishes engineering standards, identifies high-ROI automation opportunities, and maintains the technology roadmap. Provides hands-on technical direction to distributed engineers while partnering with business stakeholders to deliver scalable, production-grade solutions.

Build and deliver enterprise AI agent solutions using Microsoft Copilot Studio, Microsoft Foundry, Microsoft 365 Copilot, Azure, and Power Platform. Design agent architectures, integrations, grounding, evaluations, automations, and responsible AI controls. Implement governance, security, compliance, lifecycle management, ALM, DLP, identity, monitoring, and cost optimization. Advise customers, translate business requirements into production solutions, create reusable technical assets, and facilitate technical discussions across customer and internal teams.

Leads company-wide data science priorities, KPI frameworks, measurement standards, causal modeling, scenario planning, and agentic analytical automation. Builds reproducible SQL and Python workflows, validates predictive and causal relationships, establishes trusted metrics, partners with Finance, Product, Commercial, Engineering, and Data Engineering, and mentors scientists. The role drives adoption of governed self-service analytics and communicates assumptions, uncertainty, and business trade-offs to leadership.

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.

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.

Intern will identify productivity challenges and process gaps across global sales teams, prioritize improvement opportunities, and build AI-enabled solutions using Microsoft Copilot, agents, chatbots, Excel automation, and related tools. The role also supports sales process documentation, implementation planning, stakeholder collaboration, governance, and measuring efficiency improvements and business impact.

Build and deploy AI agent systems that automate complex business processes. Analyze workflows, design and configure agents, integrate AI with enterprise applications, develop connectors and APIs, and establish evaluation and monitoring systems. The role requires expertise in cloud AI services, LLMs, NLP, Python, integration platforms, conversational AI, RAG, vector databases, APIs, and SQL/NoSQL systems. The engineer will also explore emerging AI technologies and mentor junior developers and system administrators.

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.