Senior AI Engineer - Guidewire

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. 

Individual contributor responsible 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. Provides guidance to others informally and formally leads teams on a project and/or program. The focus of this position will be leading, architecting, designing, developing or integrating business applications.

JOB DESCRIPTION:

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 & Abilities  

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  

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 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 (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  

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I n certain jurisdictions, CNA is legally required to include a reasonable estimate of the compensation for this role. In District of Columbia , California, Colorado, Connecticut, Illinois, Maryland , Massachusetts, New York and Washington, the national base pay range for this job level is $72,000 to $141,000 annually. Salary determinations are based on various factors, including but not limited to, relevant work experience, skills, certifications and location. 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.  For a detailed look at CNA’s benefits, please visit cnabenefits.com.

CNA utilizes AI-enabled technology during the recruiting process. For more information, please visit our  careers page .

CNA is committed to providing reasonable accommodations to qualified individuals with disabilities in the recruitment process. To request an accommodation, please contact  leaveadministration@cna.com