Principal AI Engineer

## Principal AI Engineer Apply locations:
Chicago, IL, USAtime type:
Full time posted on:
Posted Yesterday job requisition :
R-7610

You have a clear vision of where your career can go. And we have the leadership to help you get there. At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential. Individual contributor providing the highest level of technical leadership in the design, development, and scaling of CNA's AI-native agentic engineering platform.

This role operates at the intersection of AI systems engineering, developer experience, and software delivery — building the foundational platform capabilities that enable the broad engineering organization to build, ship, and run high-quality, secure AI-native systems at the speed of AI. The focus is on designing and delivering agentic workflows, AI-augmented CI/CD pipelines, reusable skills and agent frameworks, and quality/security guardrails that make AI-accelerated delivery safe and scalable across the enterprise.
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* JOB DESCRIPTION:

**** Essential

Duties & Responsibilities
*** Performs a combination of duties in accordance with departmental guidelines:
** Acts as one of principal engineers for CNA's AI-native engineering platform, designing the end-to-end system spanning agentic coding workflows, skills and agent marketplaces, AI-augmented CI/CD pipelines, automated quality gates, and rapid environment provisioning. Leads integration of AI tooling (Claude Code, Cursor, Git Hub Copilot) into the software delivery lifecycle, ensuring these capabilities compose into a coherent, governed platform.
* Designs and builds the agentic infrastructure layer — including multi-agent orchestration patterns, sub-agent frameworks, skill authoring standards, and context engineering best practices — that enables engineering teams to operate at AI-native speed without sacrificing architectural integrity or security posture.
* Provides expert technical consultation to engineering leadership, portfolio teams, and architecture on how to adopt AI-native development practices, evaluate AI-generated code quality, and integrate agentic tooling into existing workflows. Advises on trade-offs between speed and quality, human-in-the-loop requirements, and appropriate levels of AI autonomy for different risk profiles (e.g., Sox-classified systems vs. rapid prototyping).
* Leads the technical strategy and implementation for engineering metrics platform. Consult with senior tech leadership stakeholders to provide insights in data-driven decision making.
* Acts as the senior technical resource mentoring engineers across the organization in AI-native engineering practices — including agentic coding patterns, context engineering, prompt-to-code workflows, and AI-assisted testing — raising the floor of capability so teams become self-sustaining without ongoing coaching dependency.
* Researches, evaluates, and recommends AI engineering tools, frameworks, and infrastructure (e.g., eval platforms, agent orchestration systems, environment provisioning automation) aligned with CNA's strategic direction. Leads build-vs-buy analysis for platform capabilities such as CI/CD tooling, sandbox provisioning, and LLM evaluation infrastructure.
* Partners closely with Architecture, Security, Cloud Engineering, and Data teams to ensure the AI engineering platform integrates with enterprise infrastructure (GCP/GKE, Git Hub, JFrog Artifactory), meets regulatory and compliance requirements (AI model tracking, Sox controls), and scales to support hundreds of engineers and AI pod teams across all portfolios.
* May perform additional duties as assigned.
*** Reporting Relationship
** Typically Director or above
** Skills, Knowledge & Abilities
*** Expert knowledge in AI-native software engineering practices including agentic coding workflows (Claude Code, Cursor, Git Hub Copilot), prompt and context engineering, multi-agent orchestration, MCP protocol, and skill/agent authoring patterns.
* Deep understanding of the modern software delivery lifecycle with specific expertise in how AI…