Senior AI Engineer

At CNA Insurance, the Senior AI Engineer role sits at the crossroads of software delivery and intelligent tooling. Based in Chicago with a hybrid work arrangement, this position leads the architectural design and integration of AI-powered engineering platforms across the CNA engineering community, helping teams embed AI capabilities into their dev and test workflows. The role offers a salary range of USD 72,000 to 141,000 per year and requires at least seven years of relevant experience, along with a Bachelor’s degree in Computer Science or a related discipline, or equivalent work experience.

Responsibilities

• Oversee the architecture, design, development, and integration of AI-enabled engineering platforms, applications, agents, and capabilities that support software delivery and boost developer productivity.
• Advance adoption of AI-powered development platforms across the engineering community through road shows, communities of practice, and demonstration sessions.
• Offer technical leadership and consultation on AI solution design, application integration, prompt and workflow patterns, and secure, scalable implementation approaches.
• Develop and implement robust testing and validation strategies for AI-enabled applications and platforms, including automated testing, quality assurance processes, and CI/CD integration.
• Research, evaluate, and recommend AI tools, frameworks, models, and platform capabilities to identify effective and cost-efficient solutions aligned with business and engineering needs.
• Collaborate with engineering, infrastructure, security, testing teams, and external partners to align requirements, integrate solutions, and ensure successful delivery of AI platform capabilities.
• Contribute to AI engineering strategy, architecture direction, governance, and best practices, including reusable patterns for platform development, integration, observability, and supportability.
• Support deployment, monitoring, issue resolution, and ongoing enhancement of AI-based applications and platforms in test and production environments to ensure reliability, performance, and continuous improvement.

Requirements

• Solid knowledge of AI-native development tools such as Cursor, GitHub Copilot, Claude Code, and MCPs.
• Strong technical capability for developing AI-based platforms, applications, agents, and skills.
• Experience developing EVALs and Observability platforms for AI-native solutions.
• Experience with AI model development and app design, specifically Vertex AI.
• Experience with Retrieval-Augmented Generation (RAG) pipeline architecture and development.
• Proficiency in high-level programming languages such as Python and/or TypeScript, Java, or JavaScript.
• Solid understanding of programming languages, databases, interfaces, and familiarity with alternative application development approaches.
• Advanced knowledge in designing and building integration platforms, APIs, and web services.
• Five or more years of experience with development tools including VS Code or JetBrains IDEs, Git and GitHub, npm/yarn, pip, Maven/Gradle, and Docker.
• Experience in AI-native system development life cycle and alternative technologies for application development.
• Understanding of state-of-the-art application development support software packages.
• Proficiency in at least one high-level programming language.
• Strong analytical and problem-solving abilities.
• Excellent communications and interpersonal skills with the ability to collaborate with peers, IT leadership, staff, and external partners.
• Ability to manage projects, lead teams, and mentor colleagues.
• Preferred: insurance industry knowledge.
• Preferred: experience with React or other front-end frameworks.
• Preferred: experience as an SDET or strong knowledge of test automation tools such as Playwright or Cypress.
• Bachelor's degree in Computer Science or related discipline, or equivalent work experience.
• Typically at least seven years of systems analysis and application development experience, plus some project leadership experience.
• Applicable certifications preferred.

Technologies

• Cursor
• GitHub Copilot
• Claude Code
• MCPs
• Vertex AI
• RAG (Retrieval-Augmented Generation)
• Python
• TypeScript
• Java
• JavaScript
• VS Code
• JetBrains IDEs
• Git
• GitHub
• npm
• yarn
• pip
• Maven
• Gradle
• Docker
• Playwright
• Cypress
• React

Reporting relationship

Typically Director or above