CN
CNASenior AI Engineer - Java
Salary$72k – $141k
LocationChicago, IL, USA
Typefull-time
SenioritySenior
Experience8+ yrs
Company size10,000+ people
PostedAug 21, 2026 · 1mo ago
Verified live1d ago
At a glanceSummarised by Seekless from the posting.
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
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
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
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
Bachelor's degree in computer science or related discipline (or equivalent experience)
8+ years of software engineering experience
Demonstrated experience in AI-assisted development / developer productivity transformation
Demonstrated experience in technical leadership, architecture, or team enablement roles
Experience with Guidewire platform and insurance domain is a strong plus
Experience in enterprise platforms or insurance domain is a plus
Prior exposure to Guidewire implementations preferred but not required
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
Skills
GitHub Copilot
Claude
Java
J2EE
Guidewire InsuranceSuite
Guidewire Cloud Platform
Guidewire Jutro Digital Platform
CI/CD
microservices
API
DevOps
automation
About the company
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.
About the role
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:
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Define and drive the AI-first engineering vision and strategy across development teams, promoting adoption of AI-assisted development practices
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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
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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:
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AI-assisted coding, testing, and debugging
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Automation frameworks and reusable patterns
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Improved developer experience and tooling
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Collaborate with business, product, architecture, and platform teams to align AI-driven solutions with business outcomes
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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
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Lead adoption of modern engineering practices, including automation, observability, and test-driven development
•
Evaluate and recommend emerging technologies in AI, automation, and developer productivity
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Support production readiness, troubleshooting, and continuous improvement of application performance and reliability
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(Preferred domain responsibility) Contribute to or guide implementations involving Guidewire InsuranceSuite and Digital Solutions
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Mentor and develop engineers, fostering a culture of continuous learning, innovation, and AI-driven excellence
May perform additional duties as assigned.
Reporting Relationship
Typically Director 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 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
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)
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Focuses on AI-first engineering transformation, not just development
•
Combines hands-on engineering with leadership and vision-setting
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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
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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
Legal
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 [email protected]