Senior AI Software Engineer

cna· 01460 Continental Casualty Company
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📍 Chicago, IL, USAFull time💰 USD 72K–141K
Full time01460 Continental Casualty Company

About this 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-KJ1 #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

Frequently Asked Questions

What is the salary for the Senior AI Software Engineer role at cna?
The listed salary for this Senior AI Software Engineer position at cna is USD 72K–141K. This is an Full time role.
Where is the Senior AI Software Engineer position at cna located?
This Senior AI Software Engineer role at cna is based in Chicago, IL, USA. The position is listed as on-site or hybrid. Check the full job description or apply directly to confirm the work arrangement.
Is the Senior AI Software Engineer role at cna full-time or part-time?
This is listed as a Full time position. It is posted as a Senior AI Software Engineer role in the 01460 Continental Casualty Company department at cna.
Which team or department does the Senior AI Software Engineer at cna belong to?
This Senior AI Software Engineer position is part of the 01460 Continental Casualty Company department at cna. See the full job description for more information about the team structure and responsibilities.
How do I apply for the Senior AI Software Engineer position at cna?
Click the "Apply Now" button on this page. You will be redirected to cna's official application portal hosted on workday where you can submit your application directly.
When was the Senior AI Software Engineer job at cna posted?
This Senior AI Software Engineer position at cna was posted on Jul 27, 2026. Apply as soon as possible — early applications are often reviewed first.
Senior AI Software Engineer
cna · 💰 USD 72K–141K
Apply for this role ↗

You'll be redirected to cna's official application page on Workday.