Senior AI Engineer - Guidewire

CNA Insurance is seeking a Senior AI Engineer to lead AI-first engineering across its enterprise platforms, blending hands-on leadership with governance to deliver scalable AI-enabled solutions. Guidewire experience is preferred, and the role centers on shaping AI-driven engineering practices across the organization.

Responsibilities

• Define and drive the AI-first engineering vision across development teams, promoting AI-assisted development practices.
• Lead and mentor engineering teams in using AI tools effectively and responsibly (examples include GitHub Copilot, Claude, Developer Assistants).
• 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.
• Enable teams to accelerate development through automation frameworks and reusable patterns.
• Enhance developer experience and tooling to speed up delivery.
• 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.

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.

Technologies

• GitHub Copilot
• Claude
• Cursor
• Developer Assistants
• Guidewire InsuranceSuite
• Guidewire Cloud Platform
• Guidewire Jutro Digital Platform (JDP)
• Java/J2EE

Reporting relationship

Typically Director or above

Education & Experience

Bachelor’s degree in computer science or a related discipline (or equivalent experience).

Typically, 8+ years of software engineering experience, including:

• AI-assisted development / developer productivity transformation
• Technical leadership, architecture, or team enablement roles
• Experience in enterprise platforms or the insurance domain is a plus
• Prior exposure to Guidewire implementations preferred but not required

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 the 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

• 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