Senior AI Engineer - Guidewire

Senior AI Engineer to lead AI-first engineering across CNA's enterprise platforms with hands-on leadership, governance, and delivery of scalable AI enabled solutions; Guidewire experience is preferred.

Location: Chicago, IL (hybrid) • Salary: USD 72,000 - 141,000 per year

Responsibilities

• Define and drive an AI-first engineering strategy across development teams, promoting AI-assisted development adoption
• Lead and mentor engineering teams in using AI tools such as GitHub Copilot, Claude, and 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, API-driven solutions across enterprise platforms
• Guide teams in building production-grade applications using modern principles including microservices, event-driven architecture, and CI/CD
• Enable teams to accelerate development through AI-assisted coding, testing, and debugging
• Accelerate development through automation frameworks and reusable patterns
• Improve developer experience and tooling to speed 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
• Contribute to or guide implementations involving Guidewire InsuranceSuite and Digital Solutions (preferred)
• 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 Claude, GitHub Copilot, Cursor, or similar tools
• 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 reports to Director level or higher

Education & Experience

• Bachelor’s degree in computer science or related discipline (or equivalent experience)
• Typically 8+ years of software engineering experience, including AI-assisted development and developer productivity transformation
• Technical leadership, architecture, or team enablement experience
• Experience in enterprise platforms or 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)

• Experience with Guidewire InsuranceSuite and Digital Solutions
• Exposure to Guidewire Cloud Platform and integration patterns
• Understanding of P and C insurance domain
• Experience with Guidewire Jutro Digital Platform (JDP) is a plus

Soft Skills

• Strong leadership, communication, and stakeholder management abilities
• Ability to influence without authority and drive cross-team change
• Collaborative approach across distributed and cross-functional teams

Role Differentiators

• Focuses on AI-first engineering transformation, not just development
• Combines hands-on engineering with leadership and strategic vision
• Drives organization-wide productivity gains through AI tooling and practices
• Opens opportunities to shape engineering culture, standards, and delivery models
• Flexible to apply AI engineering practices across multiple platforms beyond Guidewire