Senior AI Engineer - Guidewire

CNA Insurance • Chicago, IL

24d • $72,000 - $141,000 • Hybrid

About The Position

This role is for an individual contributor responsible for 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. The focus of this position will be leading, architecting, designing, developing, or integrating business applications, with a specific emphasis on driving an AI-first engineering vision and strategy. The role involves leading and mentoring engineering teams in the effective and responsible use of AI tools, establishing governance models, and ensuring the quality, security, and maintainability of AI-generated code. The engineer will architect and deliver scalable, cloud-native, and API-driven solutions, guide teams in building production-grade applications using modern engineering principles, and enable development acceleration through AI-assisted coding, testing, debugging, and automation frameworks. Collaboration with business, product, architecture, and platform teams is key to aligning AI-driven solutions with business outcomes. The role also involves providing technical oversight for complex programs, leading the adoption of modern engineering practices, evaluating emerging technologies, and supporting production readiness and continuous improvement. A preferred domain responsibility includes contributing to or guiding implementations involving Guidewire InsuranceSuite and Digital Solutions, as well as mentoring engineers to foster a culture of continuous learning and AI-driven excellence.

Requirements

• 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
• 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

• 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

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, 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.

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