Senior AI Engineer - Guidewire

cna· 01460 Continental Casualty Company
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📍 Chicago, IL, USAFull time💰 USD 72K–141K
Full time01460 Continental Casualty Company

About this role

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 

#LI-KJ1 #LI-HYBRID

In 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

Frequently Asked Questions

What is the salary for the Senior AI Engineer - Guidewire role at cna?
The listed salary for this Senior AI Engineer - Guidewire position at cna is USD 72K–141K. This is an Full time role.
Where is the Senior AI Engineer - Guidewire position at cna located?
This Senior AI Engineer - Guidewire role at cna is based in Chicago, IL, USA. The position is listed as on-site or hybrid. Check the full job description or apply directly to confirm the work arrangement.
Is the Senior AI Engineer - Guidewire role at cna full-time or part-time?
This is listed as a Full time position. It is posted as a Senior AI Engineer - Guidewire role in the 01460 Continental Casualty Company department at cna.
Which team or department does the Senior AI Engineer - Guidewire at cna belong to?
This Senior AI Engineer - Guidewire position is part of the 01460 Continental Casualty Company department at cna. See the full job description for more information about the team structure and responsibilities.
How do I apply for the Senior AI Engineer - Guidewire position at cna?
Click the "Apply Now" button on this page. You will be redirected to cna's official application portal hosted on workday where you can submit your application directly.
Senior AI Engineer - Guidewire
cna · 💰 USD 72K–141K
Apply for this role ↗

You'll be redirected to cna's official application page on Workday.