{"id":1666718,"url":"https://alion.io/job/cna-insurance-principal-ai-engineer-2","title":"Principal AI Engineer","company":{"id":2456,"name":"CNA","domain":"cna.com","url":"https://alion.io/company/cna-insurance","size_band":"1001-5000","is_staffing_agency":false,"employer_type":"direct","is_intermediary":false,"listed_via":null,"ats_vendor":"Workday","truth_index":{"grade":"A","score":98,"open_postings":12,"ghost_share":0,"stale_share":0.083,"repost_share":0,"time_to_fill_p50_days":44,"computed_at":"2026-10-21T05:46:15Z"}},"role":"AI/ML","role_family":"AI/ML","seniority":"lead","employment_type":"full_time","work_mode":"hybrid","remote_scope":null,"remote_scope_basis":null,"remote_working_hours":null,"hiring_geo_confidence":"structured","locations":["Chicago, United States"],"countries":["US"],"hiring_countries":[],"hiring_countries_total":0,"salary":{"min":97000,"max":189000,"currency":"USD","period":"year","gross":null,"usd_annual":189000},"salary_estimate":null,"experience_years_min":9,"visa_sponsorship":false,"relocation_package":false,"has_equity":false,"technologies":[{"name":"Agentic Workflows","optional":false},{"name":"AI Agents","optional":false},{"name":"AWS","optional":false},{"name":"CI/CD","optional":false},{"name":"Claude Code","optional":false},{"name":"Context Engineering","optional":false},{"name":"Copilot","optional":false},{"name":"Cursor","optional":false},{"name":"GCP","optional":false},{"name":"GitHub","optional":false},{"name":"GitHub Actions","optional":false},{"name":"Google GKE","optional":false},{"name":"Hallucination","optional":false},{"name":"Human-in-the-Loop","optional":false},{"name":"Kubernetes","optional":false},{"name":"LLM","optional":false},{"name":"LLM Guardrails","optional":false},{"name":"Model Context Protocol","optional":false},{"name":"Multi-Agent Systems","optional":false},{"name":"Platform Engineering","optional":false},{"name":"Terraform","optional":false}],"status":"live","first_seen_at":"2026-07-08T00:00:00Z","employer_posted_date":"2026-10-06","last_verified_at":"2026-10-21T16:07:20Z","board_verified":true,"closed_at":null,"days_open":105,"trust":{"level":"ok","repost_count":0,"flags":[],"days_open":105},"description":"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.\nIndividual 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.JOB DESCRIPTION:\nEssential Duties & Responsibilities\nPerforms a combination of dutiesin accordance withdepartmental guidelines:\nActs 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, GitHub Copilot) into the software delivery lifecycle, ensuring these capabilities compose into a coherent, governed platform.\n\nDesigns 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 tooperateat AI-native speed without sacrificing architectural integrity or security posture.\n\nProvides 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 ontrade-offs between speed and quality, human-in-the-loop requirements, andappropriate levelsof AI autonomy for different risk profiles (e.g., Sox-classified systems vs. rapid prototyping).\n\nLeads the technical strategy and implementationforengineering metricsplatform. Consult with senior tech leadership stakeholders to provide insightsindata-driven decision making.\n\nActs 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.\n\nResearches, 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.\n\nPartners closely with Architecture, Security, Cloud Engineering, and Data teams to ensure the AI engineering platform integrates with enterprise infrastructure (GCP/GKE, GitHub,JFrogArtifactory), meets regulatory and compliance requirements (AI model tracking, Sox controls), and scales to support hundreds of engineers and AI pod teams across all portfolios.\n\nMay performadditionalduties as assigned.\nReporting Relationship\nTypicallyDirector or above\nSkills, Knowledge & Abilities\nExpert knowledge in AI-native software engineering practices including agentic coding workflows (Claude Code, Cursor, GitHub Copilot), prompt and context engineering, multi-agent orchestration, MCP protocol, and skill/agent authoring patterns.\n\nDeep understanding of the modern software delivery lifecycle with specificexpertisein how AI transforms each phase - from AI-assisted requirements and design through agentic code generation, automated testing, AI-augmented code review, and continuous deployment.\n\nProficient in building and operating CI/CD platforms (GitHub Actions or equivalent), infrastructure-as-code (Terraform), container orchestration (GKE/Kubernetes), and cloud platforms (GCP), with the ability to design pipelines that enforce quality and security gates without creating delivery bottlenecks.\n\nStrong knowledge of application security engineering including supply chain security, artifact management and curation, static/dynamic analysis, secret management, and the specific attack vectors introduced by AI-generated code (dependency hallucination, model drift, prompt injection).\n\nDemonstrated ability to design developer platforms and tooling that serve hundreds of engineers at varying skill levels - balancing power-user capability with guardrails that prevent misuse andmaintaincode quality at scale.\n\nProven ability to evaluate and integrate emerging AI technologies rapidly, with the judgmentto distinguishbetween hype and production-ready capability. Comfortable operating in a fast-moving domain where the tooling landscape changes weekly.\n\nExcellent communication skills with the ability to translate complex AI engineering concepts for both technical and non-technical audiences. Able to influence engineering culture and drive adoption of new practices across a large, diverse organization including internal teams and managed service providers.\n\nStrong analytical and problem-solving skills with an outcomes-oriented mindset - focused on measurable improvements in delivery speed, code quality, and engineering productivity rather than toolingadoptionmetrics.\n\nEducation & Experience\nBachelor's Degree withMaster'spreferred in Computer Science, AI/ML, or related discipline, or equivalent work experience.\n\nMinimum of 9 years of solid, diverse work experience in software engineering with a minimum of 6 years in application development, including significant recent experience (2+ years) building or operating AI-augmented development tools, agentic systems, or developer platforms.\n\nDemonstrated hands-on experience with LLM-based engineering tools (Claude Code, Cursor, GitHub Copilot, or equivalent) in production engineering workflows, not just experimental use.\n\nExperience in designing and scaling inner-source or platform engineering programs across large engineering organizations preferred.\n\nApplicable certifications in cloud platforms (GCP, AWS), AI/ML, or security preferred.\n\n#LI-KJ1 #LI-HYBRID\nIn certain jurisdictions, CNA is legally required to include a reasonable estimate of the compensation for this role. In District of Columbia,California, Colorado, Connecticut, Illinois,Maryland, Massachusetts,New York and Washington, the national base pay range for this job level is$97,000 to $189,000 annually. Salary determinations are based on various factors, including but not limited to, relevant work experience, skills, certifications and location. CNA offers a comprehensive and competitive benefits package to help our employees - and their family members - achieve their physical, financial, emotional and social wellbeing goals. For a detailed look at CNA’s benefits, please visit cnabenefits.com.\nCNA utilizes AI-enabled technology during the recruiting process. For more information, please visit our careers page.\nCNA is committed to providing reasonable accommodations to qualified individuals with disabilities in the recruitment process. 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