Senior AI Software Engineer

CNA Insurance

Chicago, IL, United StatesFull-time$72,000–$141,000Posted Oct 20, 2026

About the role

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 responsible for designing, building, and operationalizing AI-driven solutions that integrate seamlessly into enterprise systems. This role combines hands-on engineering, architecture, and governance, ensuring AI solutions are scalable, secure, compliant, and aligned with business objectives.

JOB DESCRIPTION:

Essential Duties & Responsibilities

Performs a combination of duties in accordance with departmental guidelines:

Design and build enterprise AI applications using LLMs, prompt workflows, RAG, and agent-based patterns

Evaluate model quality, latency, cost, safety, and business effectiveness

Implement responsible AI controls, observability, and governance for production AI systems

Partner with architects, product owners, and business teams to identify and scale high-value AI use cases

Convert prototypes into production-ready, reliable applications

Enable automation of repeatable business processes using AI

Develop APIs and microservices to expose AI capabilities

Integrate AI solutions with enterprise platforms (claims, document systems, data platforms)

Ensure scalability, resiliency, and cost optimization

Implement test automation (unit, integration, end-to-end)

Apply secure coding practices (OAuth, JWT, secrets management)

Mentor engineers and guide AI best practices

Collaborate with business units, IT, and vendors

Evaluate emerging AI technologies and recommend solutions

May perform additional duties as assigned.

Reporting Relationship

Typically, Director or above

Skills, Knowledge & Abilities

Strong programming skills in Java, Python, TypeScript, FastAPI, Spring Boot for APIs and services.

Experience using AI-enabled development tools such as GitHub Copilot, Claude Code, Cursor, and MCPs.

Experience with RAG (Retrieval-Augmented Generation) pipeline architecture and development.

Experience with agentic system design for multi-step automation (single-agent and multi-agent), including orchestration, state and memory patterns, tool integration, and safe autonomy controls (permissions, approvals, and auditability).

Experience with Google Cloud Platform (GCP), including services such as GKE, Cloud Storage, PostgreSQL, Pub/Sub, Secret Manager, BigQuery, and Vertex AI.

Advanced knowledge of designing and building integration platforms, APIs, and web services.

Experience with CI/CD automation using tools such as Docker, GKE, GitHub, and GitHub Actions.

Strong analytical, problem-solving, and communication skills

Experience with SQL/NoSQL data stores (modeling and query optimization)

Automated testing experience (unit and integration)

Working knowledge of React and front-end fundamentals (components, state, and API integration)

Strong understanding of SRE and observability fundamentals (logs, metrics, traces) and how to use them to diagnose distributed system behavior

In-depth knowledge of the system development life cycle and of system and application development technology alternatives.

Experience working in high-performing Agile teams

Excellent communication and interpersonal skills, with the ability to work effectively with peers, IT management and staff, and internal and external business partners and clients.

Preferred insurance industry knowledge.

Education & Experience

Bachelor’s degree in computer science or related discipline, or equivalent work experience.

Typically, a minimum of 7 years of systems analysis and application development experience, including 3+ years of experience building AI solutions.

Applicable certifications preferred.

LI-Hybrid

In 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 $72,000 to $141,000 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.

CNA utilizes AI-enabled technology during the recruiting process. For more information, please visit our careers page.

CNA is committed to providing reasonable accommodations to qualified individuals with disabilities in the recruitment process. To request an accommodation, please contact leaveadministration@cna.com

Responsibilities

  • Design and build enterprise AI applications using LLMs, RAG, and agent-based patterns
  • Evaluate AI solutions for quality, performance, cost, safety, and business effectiveness
  • Implement governance, security, observability, and responsible AI controls
  • Turn prototypes into scalable, production-ready applications and automate business processes
  • Develop APIs and microservices and integrate AI with enterprise platforms
  • Build automated tests and optimize systems for reliability, resiliency, and cost
  • Mentor engineers and collaborate with business, technology, and vendor partners

Qualifications

  • Bachelor’s degree in computer science or a related discipline, or equivalent work experience
  • At least 7 years of systems analysis and application development experience, including 3+ years building AI solutions
  • Strong programming skills in Java, Python, TypeScript, FastAPI, or Spring Boot
  • Experience with RAG pipelines, agentic systems, and AI-enabled development tools
  • Experience with GCP, CI/CD, containers, APIs, and SQL or NoSQL data stores
  • Knowledge of automated testing, React, secure coding, SRE, and observability
  • Strong analytical, problem-solving, communication, and collaboration skills
  • Insurance industry knowledge preferred

Benefits

  • Comprehensive benefits supporting physical, financial, emotional, and social wellbeing for employees and their families

Skills mentioned

PythonJavaFastAPIGoogle CloudRetrieval-Augmented GenerationLarge Language ModelsAI AgentsREST APIsCI/CDIntegration Testing

About CNA Insurance

CNA is one of the largest U.S. commercial property and casualty insurance companies. Backed by more than 125 years of experience, CNA provides a broad range of standard and specialized insurance products and services for businesses and professionals in the U.S., Canada and Europe.

Insurance5,001-10,000 employeesChicago, Illinois