Senior AI Engineer - Java
cnaChicago, IL
Senior AI Engineer 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.
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(Preferred domain responsibility) Contribute to or guide implementations involving Guidewire InsuranceSuite and Digital Solutions
- 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 & AbilitiesAI 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 SkillsFull-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 SkillsStrong 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
Matching similar jobs
Level
Lead L6
Location
Chicago, IL
Occupation
Software Developers
Industry
Custom Computer Programming Services
Posted
9 days ago