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6d ago

Senior AI Engineer - Guidewire

CNA Insurance Chicago, IL

Chicago, IL

6d ago

$72k - $141k/yr Full time Ai Governance Artificial Intelligence Engineer

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Job Description

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

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