CNA Insurance

Aug 21, 2026

Senior AI Engineer - Java

HybridUnited States

Chicago, Illinois, United States

JavaGo

About the opportunity

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.

We are looking for a Senior AI Engineer to drive adoption of AI-first software delivery practices across enterprise platforms. This role is responsible for designing, guiding, and delivering AI-enabled, cloud-native solutions, while enabling teams to effectively leverage AI-assisted engineering tools to improve productivity, quality, and speed of delivery.

This is a hands-on leadership role that combines strong engineering fundamentals with the ability to set vision, establish standards, and mentor teams in adopting AI-driven development practices. Experience with Guidewire platform and insurance domain is a strong plus.

JOB DESCRIPTION

Essential Duties & Responsibilities

Performs a combination of duties in accordance with departmental 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

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

May perform additional duties as assigned.

(Preferred domain responsibility) Contribute to or guide implementations involving Guidewire InsuranceSuite and Digital Solutions

Guidewire & Domain (Preferred / Nice to Have)

Experience with Guidewire InsuranceSuite and Digital

Exposure to Guidewire Cloud Platform and integration patterns

Understanding of P&C insurance domain

Experience with Guidewire Jutro Digital Platform (JDP) is a plus

Experience in enterprise platforms or insurance domain is a plus

Prior exposure to Guidewire implementations preferred but not required

Reporting Relationship

Typically Director or above

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

#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 utilizes AI-enabled technology during the recruiting process. For more information, please visit our careers page cna.com/careers.

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 [leaveadministration@cna.com]

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

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

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

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 cnabenefits.com.

Languages

Senior AI Engineer - Java

About the opportunity

JOB DESCRIPTION

Essential Duties & Responsibilities

Guidewire & Domain (Preferred / Nice to Have)

Reporting Relationship

Role Differentiators (What Makes This Role Unique)

Skills, Knowledge & Abilities

AI Engineering & Leadership

Architecture & Modern Engineering

Technical Skills

Soft Skills

Education & Experience

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