Chicago, Illinois, United States · Hybrid
$97k–$189k/yr
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 …
Skills: AI-Native Engineering, Agentic System Design, LLM Integration, Multi-Agent Orchestration, Context Engineering
Rolling Meadows, Illinois, United States · On-site
$88k–$131k/yr
RELOCATION ASSISTANCE: Relocation assistance may be available CLEARANCE REQUIRED FOR START: Yes CLEARANCE TYPE: Secret TRAVEL: Yes, 10% of the TimeDescription At Northrop Grumman, our employees have incredible opportunit…
Skills: Systems Engineering, Model-Based Systems Engineering, SysML, MATLAB, C++
Rolling Meadows, Illinois, United States · On-site
$109k–$204k/yr
RELOCATION ASSISTANCE: Relocation assistance may be available CLEARANCE REQUIRED FOR START: Yes CLEARANCE TYPE: Top Secret TRAVEL: Yes, 10% of the TimeDescription At Northrop Grumman, our employees have incredible opport…
Skills: Systems Engineering, Model-Based Systems Engineering, SysML, MATLAB, C++
Rolling Meadows, Illinois, United States · On-site
$109k–$204k/yr
RELOCATION ASSISTANCE: Relocation assistance may be available CLEARANCE REQUIRED FOR START: Yes CLEARANCE TYPE: SAP TRAVEL: Yes, 10% of the TimeDescription At Northrop Grumman, our employees have incredible opportunities…
Skills: Systems Engineering, Model-Based Systems Engineering, SysML, MATLAB, C++
Chicago, Illinois, United States · Remote OK
$120k–$135k/yr
Job Title: Senior DevOps Engineer Company: Snapsheet Job Location: Remote Job Type: Full-time About Snapsheet: Snapsheet is claims technology the way it should be: purposeful, precise, and designed to deliver outcomes. W…
Skills: Aws, Terraform, Infrastructure as Code, Cloud Networking, Database Administration
Berwyn, Illinois, United States · Hybrid
$80k–$100k/yr
***Candidates must be authorized to work in the United States without sponsorship now or in the future*** ***Individuals MUST be local to Chicago, as relocation assistance is not available*** seoClarity is seeking a tech…
Skills: Technical Pre-sales, Software Demonstrations, Enterprise SEO, AI Search, B2B Sales Cycle
Lisle, Illinois, United States · On-site
$90k–$190k/yr
Job Title: Software Engineer Job Category: Engineering Time Type: Full time Minimum Clearance Required to Start: None Employee Type: Regular Percentage of Travel Required: Up to 10% Type of Travel: Local * * * The Opport…
Skills: C, C++, Python, RTOS, Firmware
Chicago, Illinois, United States · Hybrid
$90k–$115k/yr
We offer a flexible working policy that supports a healthy balance between personal and professional well-being. This role requires in-office presence on Tuesdays & Thursdays to collaborate, connect, and learn from peers…
Skills: Microsoft Entra ID, SSO Integration, SAML 2.0, OAuth 2.0, OIDC
Centennial, Colorado, United States · On-site
$157k–$290k/yr
When you’re the best, we’re the best. We instill an environment where employees feel engaged, satisfied and able to contribute their unique skills and talents while living and working as their authentic selves. We provid…
Skills: Software Engineering, Rapid Prototyping, Cloud-Native Platforms, Enterprise Software Development, Cross-functional Collaboration
Rolling Meadows, Illinois, United States · On-site
$88k–$131k/yr
RELOCATION ASSISTANCE: Relocation assistance may be available CLEARANCE REQUIRED FOR START: Yes CLEARANCE TYPE: Secret TRAVEL: Yes, 10% of the TimeDescription At Northrop Grumman, our employees have incredible opportunit…
Skills: Systems Engineering, Model-Based Systems Engineering, SysML, MATLAB, C++
Rolling Meadows, Illinois, United States · On-site
$109k–$204k/yr
RELOCATION ASSISTANCE: Relocation assistance may be available CLEARANCE REQUIRED FOR START: Yes CLEARANCE TYPE: SAP TRAVEL: Yes, 10% of the TimeDescription At Northrop Grumman, our employees have incredible opportunities…
Skills: Systems Engineering, Model-Based Systems Engineering, SysML, MATLAB, C++
Rolling Meadows, Illinois, United States · On-site
$109k–$204k/yr
RELOCATION ASSISTANCE: Relocation assistance may be available CLEARANCE REQUIRED FOR START: Yes CLEARANCE TYPE: Top Secret TRAVEL: Yes, 10% of the TimeDescription At Northrop Grumman, our employees have incredible opport…
Skills: Systems Engineering, Model-Based Systems Engineering, SysML, MATLAB, C++
Rolling Meadows, Illinois, United States · On-site
$88k–$131k/yr
RELOCATION ASSISTANCE: Relocation assistance may be available CLEARANCE REQUIRED FOR START: Yes CLEARANCE TYPE: Secret TRAVEL: Yes, 10% of the TimeDescription At Northrop Grumman, our employees have incredible opportunit…
Skills: Systems Engineering, Model-Based Systems Engineering, SysML, MATLAB, C++
Berwyn, Illinois, United States · Hybrid
$75k–$85k/yr
seoClarity is seeking a highly polished, commercially driven, and SaaS-experienced Senior Account Manager, Expansions & Renewals (SaaS) (Chicago-based) to join our growing team in our downtown Chicago office. We’re looki…
Skills: Account Management, Renewals Management, Upselling, Cross-selling, Customer Retention
Chicago, Illinois, United States · Remote OK
$145k–$170k/yr
Huron is a global consultancy that collaborates with clients to drive strategic growth, ignite innovation and navigate constant change. Through a combination of strategy, expertise and creativity, we help clients acceler…
Skills: Databricks, Lakehouse Architecture, Unity Catalog, Delta Lake, Mosaic AI
Rosemont, Illinois, United States · On-site
$117k–$158k/yr
Wintrust provides community and commercial banking, specialty finance and wealth management services through its 16 bank charters and nine non-bank businesses. Wintrust delivers the sophisticated solutions of a large ban…
Skills: Cloud Security Architecture, Threat Modeling, Identity And Access Management, SaaS Security, PaaS Security
Vernon Hills, Illinois, United States · On-site
$105k–$130k/yr
Position Summary This position is primarily focused on the technical aspects of product management. The candidate will have a great understanding of the product’s technical components and inner workings. They will have a…
Skills: Product Management, Technical Specifications, Software Development Lifecycle, Business Process Improvement, Project Management
Illinois, United States · Remote OK
$79k–$135k/yr
At Associated Bank we strive to create an inclusive culture where different perspectives are valued and recognized as strengths critical to our success. If you thrive in an environment where your growth and development a…
Skills: Test Planning, Test Execution, Test Automation, Defect Lifecycle Management, C#
Chicago, Illinois, United States · Hybrid
$120k–$160k/yr
Choosing Capgemini means choosing a company where you will be empowered to shape your career in the way you’d like, where you’ll be supported and inspired by a collaborative community of colleagues around the world, and …
Skills: Power BI, SQL, Data modeling, DAX, Snowflake
Chicago, Illinois, United States · Remote OK
$72k–$141k/yr
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 …
Skills: Data Science, Agile Methodology, Product Ownership, AI, Google Cloud
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Lead the design and scaling of AI-native engineering solutions and agentic systems within the Underwriting and Operations portfolio. Establish durable AI engineering practices and mentor technical talent to industrialize AI capabilities into enterprise-grade services.
Requires a Bachelor's degree in Computer Science or Engineering and at least 10 years of software engineering experience, including 3 years in a senior leadership role. Must have demonstrated experience deploying agentic AI systems in production environments, preferably within the insurance or financial services sector.
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 providing the highest level of leadership in AI-native engineering, agentic system design, and applied AI solution development across CNA's Underwriting and Operations portfolio. This position has a deep understanding of AI engineering platforms, large language model (LLM) tooling, and enterprise software delivery from an end-to-end perspective. The focus of this position is designing and scaling AI-enabled solutions that integrate into underwriting workflows, drive measurable business impact, and establish durable AI engineering practices across the organization.Essential Duties & Responsibilities
Performs a combination of duties in accordance with departmental guidelines:
Leads the scaling of AI solutions within the Underwriting portfolio, ensuring AI capabilities developed in product pods are industrialized into reliable, reusable, enterprise-grade services that integrate seamlessly into underwriting and operations workflows.
Partners closely with underwriting, operations, and product teams to translate domain-specific workflows into AI-enabled solutions — including submission intake, risk triage, data enrichment, pricing signals, and decision support — ensuring alignment to real-world underwriting processes and measurable business impact.
Designs AI integration patterns across core underwriting and operations systems — including underwriting workbench platforms and document processing pipelines — ensuring solutions are performant, scalable, and embedded directly into decisioning workflows.
Acts as a senior technical mentor, developing engineers across the organization in AI-native practices including agentic coding patterns, context engineering, prompt-to-code workflows, and AI-assisted testing. Builds durable, self-sustaining team capability without ongoing coaching dependency.
Establishes patterns for AI governance, explainability, and auditability in underwriting use cases, ensuring AI-driven decisions meet regulatory, compliance, and internal risk management expectations.
Drives reusability and cross-business-unit scalability of AI solutions, designing capabilities that can be leveraged across underwriting segments while accounting for differences in data, workflows, and risk profiles.
Researches, evaluates, and recommends AI engineering tools, frameworks, and infrastructure (e.g., eval platforms, agent orchestration systems, environment provisioning automation), supporting build-vs-buy decisions with a focus on long-term scalability and maintainability.
May perform additional duties as assigned.
Reporting Relationship
Typically Director or above
Skills, Knowledge & Abilities
Expert knowledge of AI-native engineering practices, including agentic system design, LLM integration, multi-agent orchestration, and context engineering.
Deep understanding of enterprise software delivery, including CI/CD pipelines, automated quality gates, cloud-native architecture, and production-grade system design.
Strong ability to translate complex business workflows — particularly in commercial insurance underwriting — into reliable, scalable AI-enabled solutions.
Demonstrated ability to advise on AI governance, model explainability, and regulatory compliance considerations in high-stakes or regulated environments.
Excellent analytical and problem-solving skills with the ability to evaluate build-vs-buy trade-offs and make sound architectural recommendations.
Proven ability to mentor and develop engineering talent, raising organizational capability in emerging AI practices.
Excellent communication and interpersonal skills with the ability to engage effectively with peers, technical leadership, and non-technical business stakeholders.
Working knowledge of the commercial insurance underwriting lifecycle, including submission intake, risk triage and appetite matching, underwriting analysis, and quote-to-bind processes.
Ability to translate underwriting judgment and business rules into AI-driven insights, model features, decision frameworks, and explainable outputs that can be trusted and adopted by underwriters.
Familiarity with regulatory and governance considerations impacting AI in insurance, including auditability, transparency, and appropriate use of AI in decisioning.
Education & Experience
Bachelor's degree in Computer Science, Engineering, or a related field required; Master's degree preferred.
Typically a minimum of 10 years of software engineering experience, with at least 3 years in a principal, staff, or architect-level role.
Demonstrated experience designing and deploying agentic AI systems or AI-native developer platforms in production environments.
Experience in commercial insurance or financial services, with familiarity in underwriting lifecycle processes, preferred.
Applicable certifications in AI, cloud, or related disciplines preferred.
#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 $97,000 to $189,000 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 [email protected]
CNA is one of the largest U.S. commercial property and casualty insurance companies. Backed by more than 125 years of experience, CNA provides a broad range of standard and specialized insurance products and services for businesses and professionals in the U.S., Canada and Europe.
Offices: 151 N Franklin St, Chicago, Illinois 60606, US
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