Senior AI Engineer - Guidewire

CNA Insurance invites a senior AI engineer to join our Chicago area team in a hybrid role. This position centers on an AI first engineering transformation, steering the architecture and delivery of scalable AI enabled solutions across enterprise platforms, including Guidewire offerings. You will provide technical leadership and mentorship across teams, shaping engineering culture toward AI driven excellence. The role offers a competitive salary range of USD 72,000 to 141,000 per year and a path to influence engineering standards, governance, and productivity at scale.

Responsibilities

• Define and advance the AI first engineering vision across development teams, promoting AI assisted development practices
• Lead and mentor engineers in using AI tools responsibly and effectively (eg, GitHub Copilot, Claude, Developer Assistants)
• Establish governance models and best practices for AI assisted development to ensure quality, security, compliance, and maintainability of generated code
• Apply 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 such as microservices, event driven architecture, and CI/CD
• Accelerate development through AI assisted coding, testing, debugging, automation frameworks, reusable patterns, and improved developer 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 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) Contribute to or guide implementations involving Guidewire InsuranceSuite and Digital Solutions
• Mentor engineers and foster 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
• 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
• 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

Technologies

• GitHub Copilot, Claude, Cursor
• Guidewire InsuranceSuite, Guidewire Digital Solutions
• Guidewire Cloud Platform, Guidewire Jutro Digital Platform (JDP)
• Java/J2EE, UI frameworks

Reporting relationship

Typically Director or above

AI Engineering & Leadership

• Proven experience driving AI assisted development practices at scale
• Hands on experience with 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 the P and 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

• Focus on AI first engineering transformation rather than solely development
• Combines hands on engineering with leadership and vision setting
• Opens opportunities to influence engineering culture, standards, and delivery models
• Flexible application of 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 AI assisted development
• Experience in 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