Senior AI Engineer - Guidewire

CNA • Chicago, IL

13d • Hybrid

About The Position

CNA is seeking a Senior AI Engineer to lead the adoption of AI-first software delivery practices across enterprise platforms. This role involves designing, guiding, and delivering AI-enabled, cloud-native solutions, and empowering teams to use AI-assisted engineering tools to enhance productivity, quality, and delivery speed. It is a hands-on leadership position requiring strong engineering fundamentals, vision-setting, standard establishment, and mentorship in AI-driven development practices. Experience with the Guidewire platform and the insurance domain is highly advantageous.

Requirements

• 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).
• Typically, 8+ years of software engineering experience, including: Demonstrated experience in AI-assisted development / developer productivity transformation, Technical leadership, architecture, or team enablement roles.

Nice To Haves

• Experience with Guidewire platform and insurance domain is a strong plus.
• Experience with Guidewire InsuranceSuite and Digital Solutions.
• 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.

Responsibilities

• 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, and 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.
• 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.

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior