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Chicago senior manager staff software engineering

2 senior manager staff software engineering jobs found in Chicago

CNA
01/28/2026  
Senior Software Engineer
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.  We are looking for a highly skilled Senior Python AI Developer with deep expertise in building intelligent agents using Google Vertex AI, particularly with Gemini or OpenAI models. The ideal candidate has a strong foundation in Large Language Models and understands how they work under the hood, combined with experience in evaluating model performance through structured testing methodologies. This role requires proficiency in the technical aspects of agent development while adhering to best practices in prompt engineering, context filtering, and security-aware prompting. The candidate should also have hands-on experience with modern agent frameworks and observability tools, ensuring robust,...
CNA Chicago, IL, USA Full Time
CNA
01/07/2026  
Principal Software Engineer (Guidewire)
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.  Join our team as a Principal Software Engineer and lead the design and development of cutting-edge enterprise applications and data solutions. In this role, you’ll tackle complex challenges, architect scalable integrations, and drive innovation across cloud platforms like Google Cloud and Guidewire Cloud (AWS). You’ll work at the highest technical level, applying deep expertise in SDLC, application integration, and data analytics to deliver secure, high-performing solutions. If you thrive on solving tough problems, building seamless integrations, and shaping technology strategy, we want you on our team. Experience with Guidewire, ETL processes, and cloud-native analytics is highly valued...
CNA Chicago, IL, USA Full Time

 

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