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