Weekend Manual Testing Insurance Domain Jobs in Chicago, IL

Essential Duties & Responsibilities

Performs a combination of dutiesin accordance withdepartmental 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 GuidewireInsuranceSuiteand Digital Solutions

• Mentor and develop engineers, fostering a culture of continuous learning, innovation, and AI-driven excellence

May performadditionalduties as assigned.

Reporting Relationship

TypicallyDirector 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 GuidewireInsuranceSuiteand Digital

• Exposure to Guidewire Cloud Platform and integration patterns

• Understanding of P&C insurance domain

• Experience with GuidewireJutroDigital 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