CNA Financial Corporation

Senior AI Engineer - Guidewire

CNA Financial Corporation$72K — $141K *
Information Technology
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • Bachelor's degree in computer science or related discipline, or equivalent experience
  • 8+ years of software engineering experience
  • Proven experience driving AI-assisted development practices at scale
  • Strong expertise in cloud-native architecture and microservices
  • Hands-on experience with AI tools like GitHub Copilot or Claude
  • Demonstrated ability to mentor teams in AI adoption and governance

Responsibilities

  • Define and promote the AI-first engineering vision across development teams
  • Lead and mentor engineering teams in the effective use of AI tools
  • Establish best practices for quality and governance in AI-assisted development
  • Architect scalable, cloud-native solutions for enterprise platforms
  • Guide teams in applying modern engineering principles to build applications
  • Drive integration strategies using API-first and event-driven approaches
  • Evaluate and recommend emerging technologies in AI and developer productivity

Benefits

  • Opportunity to influence engineering culture and standards
  • Flexibility to apply AI practices across multiple platforms
  • Support for continuous learning and innovation
  • Access to cutting-edge AI tools and frameworks
  • Collaboration with diverse teams across the organization
Full Job Description
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

About CNA Financial Corporation

CNA Financial Corporation provides commercial property and casualty insurance products primarily in the United States. It offers professional liability coverages and risk management services to various professional firms, including architects, real estate agents, and accounting and law firms; directors and officers, employment practices, fiduciary, and fidelity coverages to small and mid-size firms, public and privately held firms, and not-for-profit organizations; and commercial property, general liability, cyber liability, umbrella, and excess liability, as well as various other property and casualty coverages for healthcare institutions, professional services firms, and other specialized industries. The company also provides warranty and service contracts for consumer goods, and extended service contracts for consumer automobiles and recreational vehicles; and accident and health, and group life insurance products. In addition, it offers management and professional liability insurance and risk management services, as well as other specialized property and casualty coverages to various healthcare organizations, including hospitals, physician groups, and nursing homes. The company markets its products through independent agents, brokers, and general underwriters to various customers, including small, medium, and large businesses; insurance companies; associations; and other industry groups. CNA Financial Corporation was founded in 1853 and is headquartered in Chicago, Illinois.
Learn more about CNA Financial Corporation
Size
5,600 employees
Market Cap
$11.2 billion
Industry
Net Income
$690 million
Founded
1973
5 Year Trend
+4.7%
Revenue
$10.8 billion
NASDAQ

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