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Weekend Manual Testing Insurance Domain Jobs in Chicago, IL

CNA

Senior AI Engineer - Guidewire

Chicago, IL · On-site

$126K - $166K/yr

AI-assisted coding, testing, and debugging * Automation frameworks and reusable patterns * Improved ... Understanding of P&C insurance domain * Experience with Guidewire Jutro Digital Platform (JDP) is a ...

Cna

Senior AI Engineer - Guidewire

Chicago, IL

$126K - $166K/yr

AI-assisted coding, testing, and debugging * Automation frameworks and reusable patterns * Improved ... Understanding of P&C insurance domain * Experience with GuidewireJutroDigital Platform (JDP) is a ...

Perfict

Quality Assurance Lead

Chicago, IL · On-site

... testing ETL with complex transformation rules and very large data sets Preferred : • Knowledge and experience in the healthcare insurance domain Company : Perfict Global is an IT consulting ...

Flowserve

Manual Machinist 1st Shift

West Chicago, IL

$28.14 - $42.21/hr

Must be able to work overtime hours including weekends and holidays. Preferred: * 2+ years of CNC ... Life Insurance + Supplemental Life, Child, Spousal, and AD&D Insurance * Short and Long Term ...

Flowserve

Manual Machinist 1st Shift

West Chicago, IL · On-site

$28.14 - $42.21/hr

Must be able to work overtime hours including weekends and holidays. Preferred: * 2+ years of CNC ... Life Insurance + Supplemental Life, Child, Spousal, and AD&D Insurance * Short and Long Term ...

RT Specialty, LLC

Director, Business Analysis

Chicago, IL · On-site

$132K - $165K/yr

The director, business analysts will ensure accurate requirements and effective testing strategy is ... Strong domain expertise in insurance coupled with a deep knowledge of business applications ...

Ryan Specialty

Director, Business Analysis

Chicago, IL · On-site

$132K - $165K/yr

The director, business analysts will ensure accurate requirements and effective testing strategy is ... Strong domain expertise in insurance coupled with a deep knowledge of business applications ...

Ryan Specialty

Director, Business Analysis

Chicago, IL · On-site

$132K - $165K/yr

The director, business analysts will ensure accurate requirements and effective testing strategy is ... Strong domain expertise in insurance coupled with a deep knowledge of business applications ...

Ryan Specialty

Director, Business Analysis

Chicago, IL · On-site

$132K - $165K/yr

The director, business analysts will ensure accurate requirements and effective testing strategy is ... Strong domain expertise in insurance coupled with a deep knowledge of business applications ...

Wintrust

Quality Assurance Analyst

Rosemont, IL · Hybrid

$59K - $77K/yr

... and manual testing strategies across enterprise products and services. This role will focus on ... Benefits Medical Insurance Dental Vision Life insurance Accidental death and dismemberment Short ...

United Airlines

Ratabase Developer

Chicago, IL

... testing for rating changes Analyze and troubleshoot rating discrepancies production issues and ... insurance domain expertise Ability to communicate effectively with actuarial and business teams ...

Wintrust

Quality Assurance Analyst

Rosemont, IL · On-site

$59K - $77K/yr

... and manual testing strategies across enterprise products and services. This role will focus on ... Benefits Medical Insurance • Dental • Vision • Life insurance • Accidental death and ...

Deloitte

Guidewire Architect

Chicago, IL · On-site

$62.50 - $81.50/hr

Work You'll Do: As a Senior Consultant, you will bring deep technical and insurance-domain ... build, testing, deployment, and support readiness-while driving technical problem-solving ...

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As of Sep 12, 2026, the average hourly pay for weekend manual testing insurance domain in Chicago, IL is $43.17, according to ZipRecruiter salary data. Most workers in this role earn between $34.66 and $50.29 per hour, depending on experience, location, and employer.

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Weekend Manual Testing Insurance Domain jobs near you
Infographic showing various Weekend Manual Testing Insurance Domain job openings in Chicago, IL as of August 2026, with employment types broken down into 62% Full Time, 13% Part Time, and 25% Contract. Highlights an 75% In-person, and 25% Remote job distribution, with an average salary of $89,801 per year, or $43.2 per hour.

Senior AI Engineer - Guidewire

Chicago, IL • On-site

CNA
See more jobs at CNAexternal

$126K - $166K/yr

Full-time

Re-posted 27 days ago

Job description

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

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