Demo

Senior Software Engineer - AI/ML

CNA Insurance
Chicago, IL Full Time
POSTED ON 5/18/2026
AVAILABLE BEFORE 7/2/2026
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. Solid experience in AI/ML and GenAI application development, as well as experience in metrics. Preferred experience with background as SDET or deep experience with Testing tools like Playwright or Cypress etc.

JOB DESCRIPTION:

Essential Duties & Responsibilities

Performs a combination of duties in accordance with departmental guidelines:

  • Evaluates complex client area requirements and processes and designs or prepares application system specifications and develops, tests, and implements efficient and cost-effective application solutions. Includes issue resolution and on-going system maintenance.
  • May lead the integration of vendor applications and consulting resources with existing applications and resources. May hold the development lead or sub lead role on a project and/or program.
  • Acts as technical consultant to programming staff and/or business unit to mentor staff in all phases of the program development, testing and implementation process. Participates in instructing, directing, and checking the design or applications of work of others.
  • Coordinates the activities of the section with the client area and other IT areas (e.g., infrastructure, testing, and solutions).
  • Research and evaluate new, alternative solutions, and/or architecture and recommend the most efficient and cost-effective solution for the systems design, including estimating costs as necessary.
  • Acts as a liaison between clients, vendors, consulting resources, and applications area. Assists with relationship management, contract negotiations, and ensuring adherence to requirements.
  • May participate in developing recommendations for architecture direction and applications portfolio.
  • In conjunction with operations area technical staff, supports the implementation of the application into production and testing environments. May confer with technical personnel to identify and resolve issues.


May perform additional duties as assigned.

Reporting Relationship

Typically Director or above

Skills, Knowledge & Abilities

  • Solid knowledge of use of AI enabled development tools e.g. Cursor, GitHub Copilot, Claude Code, and MCPs.
  • Solid technical skills for developing AI based platforms/apps/agents/skills etc.
  • Experienced in AI/ML model development and app design, specifically Vertex AI.
  • Experience with RAG (Retrieval-Augmented Generation) pipeline architecture and development
  • Solid technical knowledge of high-level programming languages like Python and/or Typescript, Java, JavaScript,
  • Solid technical knowledge of high-level programming languages, databases, interfaces, and familiarity with application program development alternatives.
  • Advanced knowledge in designing and building Integration platforms, APIs and Webservices.
  • Working knowledge of different versions of Dev tools like VS Code or JetBrains IDEs; Git and GitHub; npm/yarn, pip, and/or maven/gradle; docker – 5 years of experience.
  • In-depth knowledge of the system development life cycle, and system and application program development technological alternatives.
  • Proven understanding of state-of-the-art application development support software packages,
  • proficiency in at least one higher level programming language.
  • Proven solid analytical and problem-solving skills.
  • Excellent communications and interpersonal skills and the ability to work effectively with peers, IT management and staff, and internal/external business partners/clients.
  • Ability to manage projects, lead teams, and mentor individuals.
  • Preferred insurance industry knowledge.
  • Preferred experience with React or other front-end frameworks.
  • Preferred experience as an SDET or deep knowledge of test automation tools like Playwright, Cypress


Education & Experience

  • Bachelor's degree in Computer Science, or related discipline, or equivalent work experience.
  • Typically a minimum of 7 years of systems analysis and application program development experience.
  • Some previous project leadership experience.
  • Applicable certifications preferred.


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 is committed to providing reasonable accommodations to qualified individuals with disabilities in the recruitment process. To request an accommodation, please contact leaveadministration@cna.com.

Salary : $72,000 - $141,000

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