16 lead software development engineer jobs found in Chicago

Job Description   Amazing Career Moments Happen Here     Transforming the insurance industry is ambitious, we know. That’s why at Applied, we’re building a team that shows up every day ready to learn, willing to try new things, and driven to deliver innovative software and services that make us indispensable to our customers – all within a culture built on values that make us indispensable to each other too. With 40+ years of experience in the Insurtech game, we’re not just redefining what’s achievable; we’re creating a place where amazing career moments are made possible.        Position Overview    We’re searching for a AI Enablement Services Lead to join our Professional Services team (Implementation, PMO, Data, Customer Success) in a hybrid location from our Chicago office. As the AI Enablement Services Lead, you will be the architect of the "Next-Gen Professional Services" organization. You are responsible for identifying, building, and...

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 DevX Software Engineer is a hands-on individual contributor focused on improving developer experience (DevX), CI/CD platforms, and cloud-native delivery pipelines. This role provides deep technical expertise across build, test, release, and reliability domains while partnering closely with application teams, SRE, security, and platform engineering. The engineer acts as an influential collaborator, enabling teams to deliver software faster, safer, and more reliably through well-designed automation and tooling. JOB DESCRIPTION: Essential Duties & Responsibilities Performs a combination of duties in accordance with departmental guidelines: Evaluate complex engineering and...

Senior Staff Software Engineer - IE07HE Staff Software Engineer - IE07IE We’re determined to make a difference and are proud to be an insurance company that goes well beyond coverages and policies. Working here means having every opportunity to achieve your goals – and to help others accomplish theirs, too. Join our team as we help shape the future.           Hartford’s Employee Benefits IT Team is seeking a highly motivated, experienced IT professional who is responsible for leading engineering teams to successfully drive the transformation of Employee Benefits application landscape.  This is a hands-on technical leadership role, that will be part of an EB IT team partnering with value stream business to drive and achieve outcomes on a multiyear transformational program. Successful candidates will be expected to demonstrate strong technical and leadership skills, excellent partnership, proven experience in delivering quality technical...

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 &...

Salary range is: $106,277.25 - $145,000.00 This position is bonus and/or commission eligible. CCC Intelligent Solutions Inc. (CCC) is a leading cloud platform for the multi-trillion-dollar insurance economy , creating intelligent experiences for insurers, repairers, automakers, part suppliers, and more. At CCC, we’re making life just work by empowering more than 35,000 businesses with industry-leading technology to get drivers back on the road and to health quickly and seamlessly. We’re pushing boundaries with innovative AI solutions that simplify and enhance the claims and repair journey. Through purposeful innovation and the strength of its connections, CCC technologies empower the people and industry relied upon to keep lives moving forward when it matters most. Learn more about CCC at www.cccis.com .   The Role The Senior Software Engineer on the CCC Workflow team will be responsible for executing the design and development of existing and new CCC Products. He...

Position Summary The Lead Quality Engineer is responsible for providing technical leadership and oversight of quality assurance activities. This role ensures consistent application of QA standards, drives test automation strategy, and partners with cross-functional teams to deliver high‑quality software releases. What will your job entail? Responsibilities: Works with product owners to obtain and analyze development requirements and coordinate clear and transparent testing and quality strategy. Lead day‑to‑day work and development of QA team members Develop and maintain test strategy, test plans, and quality benchmarks Oversee test case creation, execution, and reviews Lead defect management, root cause analysis, and quality risk reporting Drive automation initiatives across UI, API, and integration testing Integrate automated tests within CI/CD pipelines Deliver quality metrics, dashboards, and release readiness assessments Partner with...

Salary range is: $119,030.52 - $160,000.00 This position is bonus and/or commission eligible. CCC Intelligent Solutions Inc. (CCC) is a leading cloud platform for the multi-trillion-dollar insurance economy , creating intelligent experiences for insurers, repairers, automakers, part suppliers, and more. At CCC, we’re making life just work by empowering more than 35,000 businesses with industry-leading technology to get drivers back on the road and to health quickly and seamlessly. We’re pushing boundaries with innovative AI solutions that simplify and enhance the claims and repair journey. Through purposeful innovation and the strength of its connections, CCC technologies empower the people and industry relied upon to keep lives moving forward when it matters most. Learn more about CCC at www.cccis.com .   The Role CCC Intelligent Solutions is seeking a Lead Guidewire Software Engineer to drive the design, development, and delivery of scalable Guidewire ClaimCenter...

Senior Staff Software Engineer - IE07HE We’re determined to make a difference and are proud to be an insurance company that goes well beyond coverages and policies. Working here means having every opportunity to achieve your goals – and to help others accomplish theirs, too. Join our team as we help shape the future.              Senior IT Engineer – Full Stack Developer Join the Digital Enablement Value Stream team as a Senior IT Engineer (Full Stack Developer). In this strategic role, you’ll be at the forefront of our modernization initiative, leading the transformation of our legacy portfolio of customer communication services onto AWS and industry leading platforms. You’ll collaborate with architects, product owners, and cross-functional teams to deliver innovative, scalable, and cloud-native enterprise solutions that enhance customer engagement and operational efficiency. Key Responsibilities Lead the design, development, and deployment of full...

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...

RT Specialty, a division of Ryan Specialty, is a leading wholesale distributor of specialty insurance products and services. Our experienced brokers are specialized in property, casualty, professional lines, transportation and workers’ compensation, providing creative solutions to retail brokerage firms. We define ourselves through our superior execution on behalf of our clients, which has established us as a leader in the industry. Position Summary Ryan Specialty is looking for a Senior UX Designer to join our team. Our UX Design team within the Digital Solutions group shapes user experiences across RT Specialty’s ecosystem of digital products, including internal tools and client‑facing platforms. This position offers a hybrid schedule with three days in the office and two days working from home in our Chicago, IL or Buffalo, NY locations. We are looking for a Senior UX Designer, with “full-stack” skills (UI + UX/IA + UX research) skills – strong UI skills are a must....

Position Summary The Director of Data Engineering is responsible for building and operating the data engineering function within Ryan Specialty’s corporate data organization. This role is accountable for the silver and gold layer of the medallion data architecture thus transforming raw ingested data into clean, conformed, and business-ready data assets that serve as the foundation for downstream consumption. Beyond technical delivery, this role builds and scales a high-performing engineering team, establishes disciplined software development practices, and manages the contractor and external parties that augment internal capacity. An ideal candidate should be collaborative and dynamic and be able to work across the organization on a fast-paced and quickly evolving team. The leader will have five primary responsibilities: 1. Own and deliver the silver and gold layer of the medallion data architecture 2. Establish and enforce a standardized software development lifecycle for...

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...

Salary range is: $136,885.10 - $200,000.00 This position is bonus and/or commission eligible. CCC Intelligent Solutions Inc. (CCC) is a leading cloud platform for the multi-trillion-dollar insurance economy , creating intelligent experiences for insurers, repairers, automakers, part suppliers, and more. At CCC, we’re making life just work by empowering more than 35,000 businesses with industry-leading technology to get drivers back on the road and to health quickly and seamlessly. We’re pushing boundaries with innovative AI solutions that simplify and enhance the claims and repair journey. Through purposeful innovation and the strength of its connections, CCC technologies empower the people and industry relied upon to keep lives moving forward when it matters most. Learn more about CCC at www.cccis.com .   The Role CCC is looking for a Senior Manager of the CCC data platform that will lead a team of diversely skilled database engineers who architect, build, and...

Salary range is: $136,885.10 - $200,000.00 This position is bonus and/or commission eligible. CCC Intelligent Solutions Inc. (CCC) is a leading cloud platform for the multi-trillion-dollar insurance economy , creating intelligent experiences for insurers, repairers, automakers, part suppliers, and more. At CCC, we’re making life just work by empowering more than 35,000 businesses with industry-leading technology to get drivers back on the road and to health quickly and seamlessly. We’re pushing boundaries with innovative AI solutions that simplify and enhance the claims and repair journey. Through purposeful innovation and the strength of its connections, CCC technologies empower the people and industry relied upon to keep lives moving forward when it matters most. Learn more about CCC at www.cccis.com .   The Role We are seeking a Senior Manager to lead our Full Stack Engineering team in Subrogation. This role is critical to delivering high-quality, scalable web...

Salary range is: $136,885.10 - $200,000.00 This position is bonus and/or commission eligible. CCC Intelligent Solutions Inc. (CCC) is a leading cloud platform for the multi-trillion-dollar insurance economy , creating intelligent experiences for insurers, repairers, automakers, part suppliers, and more. At CCC, we’re making life just work by empowering more than 35,000 businesses with industry-leading technology to get drivers back on the road and to health quickly and seamlessly. We’re pushing boundaries with innovative AI solutions that simplify and enhance the claims and repair journey. Through purposeful innovation and the strength of its connections, CCC technologies empower the people and industry relied upon to keep lives moving forward when it matters most. Learn more about CCC at www.cccis.com .   The Role We are seeking a Senior Manager to lead our Machine Learning (ML) team in the subrogation business. This role is critical to expanding the emerging...

ABOUT HUB At HUB International , we are a team of entrepreneurs. We believe in protecting and supporting the aspirations of individuals, families, and businesses. We help our clients evaluate their risks and develop solutions tailored to their needs. We believe in empowering our employees to learn, grow, and make a difference. Our structure enables our teams to maintain their own unique, regional culture while leveraging support and resources from our corporate centers of excellence.  HUB is one of the largest global insurance and employee benefits broker, providing a boundaryless array of business insurance, employee benefits, risk services, personal insurance, retirement, and private wealth management products and services. With over $5 billion in revenue and almost 20,000 employees in 600 offices throughout North America, HUB has grown substantially, in part due to our industry leading success in mergers and acquisitions.  ABOUT SPECIALTY PROGRAM GROUP (SPG)...