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director of software engineering Illinois

37 director of software engineering jobs found

Allstate
08/16/2026  
Principal Engineer, Developer Experience
At Allstate, great things happen when our people work together to protect families and their belongings from life’s uncertainties. And for more than 90 years, our innovative drive has kept us a step ahead of our customers’ evolving needs. From advocating for seat belts, air bags and graduated driving laws, to being an industry leader in pricing sophistication, telematics, and, more recently, device and identity protection.  Job Description The Principal Engineer leads Allstate's Developer Experience organization, driving the technical strategy, adoption, and continuous improvement of the tools, platforms, and capabilities engineers use to build, test, deploy, secure, and operate software. As a hands-on technical leader and advocate for the developer community, this individual partners closely with engineering teams to reduce friction, improve productivity, and enhance the overall development experience. The Principal Engineer champions modern engineering practices,...
Allstate IL Full Time
Sedgwick
08/11/2026  
Director IT Applications
By joining Sedgwick, you'll be part of something truly meaningful. It’s what our 33,000 colleagues do every day for people around the world who are facing the unexpected. We invite you to grow your career with us, experience our caring culture, and enjoy work-life balance. Here, there’s no limit to what you can achieve. Newsweek Recognizes Sedgwick as America’s Greatest Workplaces National Top Companies Certified as a Great Place to Work® Fortune Best Workplaces in Financial Services & Insurance Director IT Applications Director, IT Applications Sedgwick Repair Solutions Position Summary The Director of IT Applications is responsible for the strategic leadership, development, implementation, and support of business applications supporting Sedgwick Repair Solutions' property repair business. This role leads a team of developers, analysts, and third-party partners responsible for delivering scalable technology solutions that support contractor networks,...
Sedgwick Elgin, IL Full Time
Markel
08/11/2026  
Executive Loss Control, Property & Marine Specialist
What part will you play? If you’re looking for a place where you can make a meaningful difference, you’ve found it. The work we do at Markel gives people the confidence to move forward and seize opportunities, and you’ll find your fit amongst our global community of optimists and problem-solvers. We’re always pushing each other to go further because we believe that when we realize our potential, we can help others reach theirs. Join us and play your part in something special! The Executive Risk Solution Specialist is a senior-level technical position supporting loss control/risk engineering efforts through interaction with internal and external stakeholders. The Specialist will possess a strong property and inland marine risk control background to support Markel’s property, inland marine, and ocean marine book of business. Build relationships  Partner with Underwriting to select, retain, and grow a profitable book of business to meet department and corporate goals for...
Markel Chicago, IL Full Time
CNA
07/28/2026  
Senior AI 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.  Individual contributor responsible for designing, building, and operationalizing AI-driven solutions that integrate seamlessly into enterprise systems. This role combines hands-on engineering, architecture, and governance, ensuring AI solutions are scalable, secure, compliant, and aligned with business objectives. JOB DESCRIPTION: Essential Duties & Responsibilities Performs a combination of duties in accordance with departmental guidelines: Design and build enterprise AI applications using LLMs, prompt workflows, RAG, and agent-based patterns   Evaluate model quality, latency, cost, safety, and business effectiveness   Implement responsible AI...
CNA Chicago, IL Full Time
RLI
07/27/2026  
IT Director - AI
About Us  We’re not like other insurance companies. From our specialty products to our business model, our culture to our results — we’re different. Different is who we are, and how we work, interact, deliver and succeed together. Creating a different and better insurance experience doesn’t just happen. It takes focus and a shared passion for going beyond the expected to forge relationships and deliver care that makes a difference. This approach rises from and is supported by our talented, ethical and smart team of employee owners united around a single purpose: to work alongside our customers and partners when they need us, in unexpected ways, with exceptional results. Apply today to make a difference with us.  RLI is a Glassdoor Best Places to Work company with a strong, successful background. For decades, our financial track record has been stellar — a testament to our culture and validation of our reputation as an excellent underwriting company....
RLI Chicago, IL Full Time
CNA
06/27/2026  
Senior Data Analytics Consultant - Underwriting Portfolio Management
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.  Consider joining CNA Insurance’s Portfolio Management Data Analytics team, which partners closely with Underwriting and business leadership to drive strategy execution, accountability, and profitable growth through analytics and insight. This team leverages data and analytics synthesized from across the organization to ensure underwriting strategies are effectively translated into measurable actions and outcomes. In this Senior Consultant role, you will leverage advanced analytical expertise, technical skills, and strong business partnership to drive significant impact across a variety of commercial insurance products. You will lead smaller scale initiatives to implement automated...
CNA Chicago, IL Full Time
Pet Partners Pet Insurance
06/18/2026  
Senior Engineer, Customer Web and Mobile Experience
Established in 2021,   Independence Pet Holdings   is a corporate holding company that manages a diverse and broad portfolio of modern pet health brands and services, including insurance, pet education, lost recovery services, and more throughout North America.   We believe pet insurance is more than a financial product and build solutions to simplify the pet parenting journey and help improve the well-being of pets. As a leading authority in the pet category, we operate with a full stack of resources, capital, and services to support pet parents. Our multi-brand and omni-channel approach include our own insurance carrier, insurance brands and partner brands.  Job Summary   We are seeking a Senior Engineer to design, build, and ship high-quality features across our customer-facing web and mobile platforms. Reporting to the Senior Director, Customer Web and Mobile Experience, this role is a senior individual contributor who partners with product, design, and...
Pet Partners Pet Insurance Chicago, IL Full Time
Independence Pet Group
06/18/2026  
Senior Engineer, Customer Web and Mobile Experience
Established in 2021,   Independence Pet Holdings   is a corporate holding company that manages a diverse and broad portfolio of modern pet health brands and services, including insurance, pet education, lost recovery services, and more throughout North America.   We believe pet insurance is more than a financial product and build solutions to simplify the pet parenting journey and help improve the well-being of pets. As a leading authority in the pet category, we operate with a full stack of resources, capital, and services to support pet parents. Our multi-brand and omni-channel approach include our own insurance carrier, insurance brands and partner brands.  Job Summary   We are seeking a Senior Engineer to design, build, and ship high-quality features across our customer-facing web and mobile platforms. Reporting to the Senior Director, Customer Web and Mobile Experience, this role is a senior individual contributor who partners with product, design, and...
Independence Pet Group Chicago, IL Full Time
Pet Partners Pet Insurance
06/17/2026  
Principal Engineer, Customer Web and Mobile Experience
Established in 2021,   Independence Pet Holdings   is a corporate holding company that manages a diverse and broad portfolio of modern pet health brands and services, including insurance, pet education, lost recovery services, and more throughout North America.   We believe pet insurance is more than a financial product and build solutions to simplify the pet parenting journey and help improve the well-being of pets. As a leading authority in the pet category, we operate with a full stack of resources, capital, and services to support pet parents. Our multi-brand and omni-channel approach include our own insurance carrier, insurance brands and partner brands.  Job Summary   We are seeking a Principal Engineer to serve as the senior-most individual contributor and technical leader for our customer-facing web and mobile platforms. Reporting to the Senior Director, Customer Web and Mobile Experience, this role sets the technical direction for the React and...
Pet Partners Pet Insurance Chicago, IL Full Time
CNA
06/17/2026  
Senior AI 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.  We are looking for a Senior AI Engineer to drive adoption of AI-first software delivery practices across enterprise platforms. This role is responsible for designing, guiding, and delivering AI-enabled, cloud-native solutions, while enabling teams to effectively leverage AI-assisted engineering tools to improve productivity, quality, and speed of delivery. This is a hands-on leadership role that combines strong engineering fundamentals with the ability to set vision, establish standards, and mentor teams in adopting AI-driven development practices. Experience with Guidewire platform and insurance domain is a strong plus. JOB DESCRIPTION: Essential Duties & Responsibilities...
CNA Chicago, IL Full Time
CNA
06/17/2026  
Senior AI 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.  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...
CNA Chicago, IL Full Time
Independence Pet Group
06/17/2026  
Principal Engineer, Customer Web and Mobile Experience
Established in 2021,   Independence Pet Holdings   is a corporate holding company that manages a diverse and broad portfolio of modern pet health brands and services, including insurance, pet education, lost recovery services, and more throughout North America.   We believe pet insurance is more than a financial product and build solutions to simplify the pet parenting journey and help improve the well-being of pets. As a leading authority in the pet category, we operate with a full stack of resources, capital, and services to support pet parents. Our multi-brand and omni-channel approach include our own insurance carrier, insurance brands and partner brands.  Job Summary   We are seeking a Principal Engineer to serve as the senior-most individual contributor and technical leader for our customer-facing web and mobile platforms. Reporting to the Senior Director, Customer Web and Mobile Experience, this role sets the technical direction for the React and...
Independence Pet Group Chicago, IL Full Time
CNA
06/12/2026  
AI Security Consulting Director
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.  The Consulting Director, AI Security is a hands-on technical contributor responsible for reviewing, evaluating, and validating AI initiatives across CNA’s enterprise. This role performs architecture and design reviews of AI, Machine Learning (ML), Generative AI (GenAI), Large Language Model (LLM), and agentic solutions; develops technology evaluation criteria for RFIs/RFPs; and tests and validates candidate solutions against security requirements. As part of the AI Governance review process, this role is a representative of the AI Security team and provides the technical security perspective on AI threats — focusing on the technical security assessment rather than governance, risk, or...
CNA Chicago, IL Full Time
CNA
06/12/2026  
Principal AI 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.  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. JOB DESCRIPTION: Essential Duties & Responsibilities   Performs a combination of...
CNA Chicago, IL Full Time
CNA
06/10/2026  
Senior AI 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.  Senior individual contributor on the Developer Experience (DevX) platform team, responsible for designing, building, and operating an AI-native software delivery platform across five capability domains: FeedBack (AI intelligence, observability, DORA metrics), Enterprise Enablement (Internal Developer Portal, golden-path onboarding), Build & Delivery (CI/CD/CT, GitHub Actions, ArgoCD, Harness), Safety / Application Security (Veracode, SonarCloud, JFrog Xray, supply-chain security), and App Accelerator (container base images, dev containers, starter app templates). Leads the development of AI agentic SDLC workflows — autonomous and human-in-the-loop agents that accelerate code generation,...
CNA Chicago, IL Full Time
CNA
06/10/2026  
Principal AI 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.  Individual contributor providing the highest level of technical leadership in the design, development, and scaling of CNA's AI-native agentic engineering platform. This role operates at the intersection of AI systems engineering, developer experience, and software delivery — building the foundational platform capabilities that enable the broad engineering organization to build, ship, and run high-quality, secure AI-native systems at the speed of AI. The focus is on designing and delivering agentic workflows, AI-augmented CI/CD pipelines, reusable skills and agent frameworks, and quality/security guardrails that make AI-accelerated delivery safe and scalable across the enterprise. JOB...
CNA Chicago, IL Full Time
CNA
06/10/2026  
System Architect Director - AI Platform Engineering
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.  The System Architect (SA) Director for AI Platforms Engineering serves as the technical owner for the enterprise AI platform which is the shared foundation powering all AI and GenAI products across the organization. This leader owns the platform's architecture, engineering standards, and delivery roadmap, translating strategic AI capabilities into reliable, scalable, and governed platform capabilities that accelerate every product team building on top of them. Working in close partnership with Enterprise Architects, Product Management, and Release Train Engineers (RTEs), the SA Director ensures that platform investments are tightly aligned to business outcomes, compliance requirements, and...
CNA Chicago, IL Full Time
CNA
06/08/2026  
AI Attack Surface and Threat Exposure Management Consulting Director
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.  The Consulting Director, Attack Surface Management defines strategy, adoption, and governance of automation, AI, and agentic AI across application security, vulnerability management, ethical hacking, and attack surface management programs. Oversees evaluation and deployment of AI-centric security solutions while establishing audit-defensible standards, processes, and secure AI development practices. Drives enterprise-scale identification, analysis, and remediation of external attack surface risk through advanced automation, analytics, and AI-enabled capabilities. Partners with senior leadership and cross-functional teams to prioritize risk, improve operational efficiency, and deliver...
CNA Chicago, IL Full Time
Crum & Forster
06/01/2026  
Regional Underwriting Director - Contract Surety
Crum & Forster Company Overview Crum & Forster (C&F) , with a proud history dating to 1822, provides specialty and standard commercial lines insurance products through our admitted and surplus lines insurance companies. C&F enjoys a financial strength rating of "A+"(Superior) by AM Best and is proud of our superior customer service platform. Our claims and risk engineering services are recognized as among the best in the industry. Our most valuable asset is our people: more than 2000 employees in locations throughout the United States. The company is increasingly winning recognition as a great place to work, earning several workplace and wellness awards, including the 2024 Great Place to Work® Award  for our employee-first focus and our steadfast commitment to diversity, equity and Inclusion. C&F is part of Fairfax Financial Holdings, a global, billion dollar organization.   For more information about Crum & Forster, please...
Crum & Forster Chicago, IL Full Time
CNA
05/27/2026  
System Architect Director - AI Innovation
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.  The System Architect (SA) Director has overall technical authority for one or more programs/Agile Release Trains (ARTs) within a portfolio, with direct management accountability for a staff of Engineers and Business Analysts. The SA Director works closely with an Enterprise Architect, Product Management and Release Train Engineer (RTE) to ensure ongoing alignment of technical and business outcomes. The SA Director owns the creation, maintenance and communication of the Architecture, along with implementation by one or more development teams. The SA Director is an expert and champion of Scaled Agile Framework (SAFe) architectural design and development, incrementally building the associated...
CNA Chicago, IL Full Time

 

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