CNA Insurance

Senior AI Engineer - Guidewire

CNA Insurance  •  $72k - $141k/yr  •  Chicago, IL (Hybrid)  •  2 hours ago
Apply
AI can make mistakes so check important info. Chat history is never stored.

Job 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.

Individual contributor responsible providing a high level of expertise in systems analysis and design, application development and/or integration, and testing of complex systems applications to support business needs. Provides guidance to others informally and formally leads teams on a project and/or program. The focus of this position will be leading, architecting, designing, developing or integrating business applications.

Essential Duties & Responsibilities

Performs a combination of dutiesin accordance withdepartmental guidelines:

  • Define and drive the AI-first engineering vision and strategy across development teams, promoting adoption of AI-assisted development practices

  • Lead and mentor engineering teams in using AI tools (e.g., GitHub Copilot, Claude, Developer Assistants) effectively and responsibly

  • Establish governance models and best practices for AI-assisted development, ensuring quality, security, compliance, and maintainability of generated code

  • Apply strong engineering judgment to review, validate, and standardize AI-generated outputs

  • Architect and deliver scalable, cloud-native and API-driven solutions across enterprise platforms

  • Guide teams in building production-grade applications using modern engineering principles (microservices, event-driven architecture, CI/CD)

  • Enable teams to accelerate development through:

  • AI-assisted coding, testing, and debugging

  • Automation frameworks and reusable patterns

  • Improved developer experience and tooling

  • Collaborate with business, product, architecture, and platform teams to align AI-driven solutions with business outcomes

  • Drive integration strategies across enterprise systems using API-first and event-driven approaches

  • Provide technical oversight and leadership for complex programs and cross-functional initiatives

  • Lead adoption of modern engineering practices, including automation, observability, and test-driven development

  • Evaluate and recommend emerging technologies in AI, automation, and developer productivity

  • Support production readiness, troubleshooting, and continuous improvement of application performance and reliability

  • (Preferred domain responsibility) Contribute to or guide implementations involving GuidewireInsuranceSuiteand Digital Solutions

  • Mentor and develop engineers, fostering a culture of continuous learning, innovation, and AI-driven excellence

May performadditionalduties as assigned.

Reporting Relationship

TypicallyDirector or above

Skills, Knowledge & Abilities

AI Engineering & Leadership

  • Proven experience driving AI-assisted development practices at scale

  • Hands-on experience with tools such as Claude, GitHub Copilot, Cursor, or similar

  • Strong ability to evaluate and govern AI-generated code

  • Demonstrated ability to define standards, frameworks, and best practices

  • Experience mentoring teams and enabling AI adoption across engineering organizations

  • Strong understanding of secure coding and compliance in AI-enabled environments

Architecture & Modern Engineering

  • Strong expertise in cloud-native architecture, microservices, and distributed systems

  • Experience with API-first, integration, and event-driven architectures

  • Proven ability to build scalable, production-grade applications

  • Familiarity with DevOps, CI/CD, and automation frameworks

Technical Skills

  • Full-stack development expertise (Java/J2EE or similar stack, microservices, UI frameworks)

  • Strong knowledge of API design, integration platforms, and web services

  • Excellent problem-solving and decision-making skills

Guidewire & Domain (Preferred / Nice to Have)

  • Experience with GuidewireInsuranceSuiteand Digital

  • Exposure to Guidewire Cloud Platform and integration patterns

  • Understanding of P&C insurance domain

  • Experience with GuidewireJutroDigital Platform (JDP) is a plus

Soft Skills

  • Strong leadership, communication, and stakeholder management skills

  • Ability to influence without authority and drive change across teams

  • Strong collaboration across distributed and cross-functional teams

Role Differentiators (What Makes This Role Unique)

  • Focuses on AI-first engineering transformation, not just development

  • Combines hands-on engineering with leadership and vision-setting

  • Enables organization-wide productivity gains using AI tools

  • Opportunity to influence engineering culture, standards, and delivery model

  • Flexibility to apply AI engineering practices across multiple platforms, not limited to Guidewire

Education & Experience

  • Bachelor’s degree in computer science or related discipline (or equivalent experience)

  • Typically, 8+ years of software engineering experience, including:

  • Demonstrated experience in:

  • AI-assisted development / developer productivity transformation

  • Technical leadership, architecture, or team enablement roles

  • Experience in enterprise platforms or insurance domain is a plus

  • Prior exposure to Guidewire implementations preferred but not required

#LI-KJ1 #LI-HYBRID

I n 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

CNA Insurance

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.

Industry
Finance & Insurance
Company Size
5,001-10,000 employees
Headquarters
Chicago, Illinois
Year Founded
Unknown
Website
cna.com
Social Media