Senior AI Engineer - Guidewire

We 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.

• 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., Git Hub 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 Insurance Suite and Digital Solutions
• Mentor and develop engineers, fostering a culture of continuous learning, innovation, and AI‑driven excellence
• May perform additional duties as assigned

Typically Director or above

• AI Engineering & Leadership:
  Proven experience driving AI‑assisted development practices at scale; hands‑on experience with tools such as Claude, Git Hub 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 Dev Ops, 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 Insurance Suite and Digital; exposure to Guidewire Cloud Platform and integration patterns; understanding of P&C insurance domain; experience with Guidewire Jutro Digital Platform (JDP) is…