Insurance Tech Jobs in Chicago, IL (NOW HIRING)

Join our AI & Engineering team in transforming technology platforms, driving innovation, and helping make a significant impact on our clients' success. You'll work alongside talented professionals reimagining and re-engineering operations and processes that are critical to businesses. Your contributions can help clients improve financial performance, accelerate new digital ventures, and fuel growth through innovation.

AI & Engineering leverages cutting-edge engineering capabilities to build, deploy, and operate integrated/verticalized sector solutions in software, data, AI, network, and hybrid cloud infrastructure. These solutions are powered by engineering for business advantage, transforming mission-critical operations. We enable clients to stay ahead with the latest advancements by transforming engineering teams and modernizing technology & data platforms. Our delivery models are tailored to meet each client's unique requirements.

Recruiting for this role ends on 06/30/2026.

Work you'll do

As a Senior Manager on the Insurance Solutions team, you will be responsible for leading end-to-end Guidewire programs across PolicyCenter, BillingCenter, and ClaimCenter, and driving market activation for our Insurance practice.

• Lead multi-release Guidewire implementations, upgrades, and Guidewire Cloud migrations from inception through hypercare, including environment strategy, release planning, and cutover execution.
• Define target-state architectures integrating Guidewire with rating, customer relationship management, document management, data, and financial systems using application programming interfaces, messaging, events, and Guidewire accelerators.
• Direct solution design and development in Gosu and Java, including product model configuration, business rules, workflows, batch processes, and plugins, and enforce coding standards and continuous integration/continuous deployment quality gates.
• Establish non-functional requirements and performance engineering strategies, and oversee data conversion, migration, and reporting and analytics design.
• Lead market activation efforts for Guidewire services, including pipeline development, offering design, pursuit support, pricing, and go-to-market asset creation, while building senior client relationships.
• Build and manage delivery teams, budgets, roadmaps, governance, risk management, vendor coordination, user acceptance testing, training, release readiness, and production support operating models.

A successful candidate would possess these skills:

• Ability to work independently and collaborate as part of a team
• Effective written and verbal communication skills
• Meticulous attention to detail and quality of work product
• Ability to build and sustain professional relationships
• Ability to lead projects or workstreams
• Ability to manage and prioritize multiple tasks in a fast-paced and dynamic environment
• Strong interpersonal skills and professional demeanor
• Ability to meet deadlines
• Ability to mentor and provide clear guidance to others

The team

Our Industry Solutions offering provides verticalized solutions that transform how clients sell products, deliver services, generate growth, and execute mission-critical operations. We deliver integrated business expertise with scalable, repeatable technology solutions specifically engineered for each sector.

Insurance moves the world forward. It's the invisible safety net behind everything else that happens in society. To stay ahead, insurers need modern solutions. Our Insurance Solutions practitioners serve as trusted advisors to our clients, combining strategic thinking with deep industry knowledge to solve complex business problems in a team-based environment. We architect operating models and processes that enable growth, optimize capital, and maximize operational efficiency. We implement innovative technology solutions spanning core, digital, data, analytics, cloud and AI.

Deloitte's Financial Services Industry consulting practice is the largest in the world, serving over 90% of Fortune 500 banking, insurance, securities, investment management, and real estate companies.

Qualifications

Required:

• Bachelor's degree in Computer Science, Engineering, or Information Systems
• 8+ years of Guidewire implementation experience, including 2+ full-lifecycle deployments of PolicyCenter, BillingCenter, and/or ClaimCenter in production
• 5+ years of Guidewire configuration and integration experience using Gosu and Java, including rules, screens, workflows, batch processes, and plugins
• 3+ years of experience leading Guidewire integration patterns using application programming interfaces, events, messaging, and web services with rating, customer relationship management, data, and document management systems
• 2+ years of experience with Guidewire Cloud or Guidewire upgrades, including development operations pipelines, environment management, and release governance
• Ability to travel 50-75%, on average, based on the work you do and the clients and industries/sectors you serve.
• Must be legally authorized to work in the United States without the need for employer sponsorship, now or at any time in the future.

Preferred:

• Guidewire certifications in PolicyCenter, BillingCenter, ClaimCenter, Integration, and/or Cloud
• Experience with cloud and development operations tools used for Guidewire, including Amazon Web Services or Microsoft Azure, Kubernetes, Terraform, GitHub Actions, Azure DevOps, Jenkins, SonarQube, and observability platforms
• Experience with Guidewire DataHub/InfoCenter, data migration tools, and analytics pipelines for underwriting, billing, and/or claims
• Experience implementing Insurance Services Office or bureau content, rating engines, and product model design for personal and/or commercial lines
• Experience with Guidewire performance engineering, including load testing, tuning, caching, and database optimization
• Experience leading global delivery teams and Agile delivery frameworks, including Scrum, Kanban, and/or Scaled Agile Framework

The wage range for this role takes into account the wide range of factors that are considered in making compensation decisions including but not limited to skill sets; experience and training; licensure and certifications; and other business and organizational needs. The disclosed range estimate has not been adjusted for the applicable geographic differential associated with the location at which the position may be filled. At Deloitte, it is not typical for an individual to be hired at or near the top of the range for their role and compensation decisions are dependent on the facts and circumstances of each case. A reasonable estimate of the current range is $180,200 to $355,100.

You may also be eligible to participate in a discretionary annual incentive program, subject to the rules governing the program, whereby an award, if any, depends on various factors, including, without limitation, individual and organizational performance.

Join our AI & Engineering team in transforming technology platforms, driving innovation, and helping make a significant impact on our clients' success. You'll work alongside talented professionals reimagining and re-engineering operations and processes that are critical to businesses. Your contributions can help clients improve financial performance, accelerate new digital ventures, and fuel growth through innovation.

AI & Engineering leverages cutting-edge engineering capabilities to build, deploy, and operate integrated/verticalized sector solutions in software, data, AI, network, and hybrid cloud infrastructure. These solutions are powered by engineering for business advantage, transforming mission-critical operations. We enable clients to stay ahead with the latest advancements by transforming engineering teams and modernizing technology & data platforms. Our delivery models are tailored to meet each client's unique requirements.

Recruiting for this role ends on 06/30/2026.

Work you'll do

As a Senior Manager on the Insurance Solutions team, you will be responsible for leading end-to-end Guidewire programs across PolicyCenter, BillingCenter, and ClaimCenter, and driving market activation for our Insurance practice.

• Lead multi-release Guidewire implementations, upgrades, and Guidewire Cloud migrations from inception through hypercare, including environment strategy, release planning, and cutover execution.
• Define target-state architectures integrating Guidewire with rating, customer relationship management, document management, data, and financial systems using application programming interfaces, messaging, events, and Guidewire accelerators.
• Direct solution design and development in Gosu and Java, including product model configuration, business rules, workflows, batch processes, and plugins, and enforce coding standards and continuous integration/continuous deployment quality gates.
• Establish non-functional requirements and performance engineering strategies, and oversee data conversion, migration, and reporting and analytics design.
• Lead market activation efforts for Guidewire services, including pipeline development, offering design, pursuit support, pricing, and go-to-market asset creation, while building senior client relationships.
• Build and manage delivery teams, budgets, roadmaps, governance, risk management, vendor coordination, user acceptance testing, training, release readiness, and production support operating models.

A successful candidate would possess these skills:

• Ability to work independently and collaborate as part of a team
• Effective written and verbal communication skills
• Meticulous attention to detail and quality of work product
• Ability to build and sustain professional relationships
• Ability to lead projects or workstreams
• Ability to manage and prioritize multiple tasks in a fast-paced and dynamic environment
• Strong interpersonal skills and professional demeanor
• Ability to meet deadlines
• Ability to mentor and provide clear guidance to others

The team

Our Industry Solutions offering provides verticalized solutions that transform how clients sell products, deliver services, generate growth, and execute mission-critical operations. We deliver integrated business expertise with scalable, repeatable technology solutions specifically engineered for each sector.

Insurance moves the world forward. It's the invisible safety net behind everything else that happens in society. To stay ahead, insurers need modern solutions. Our Insurance Solutions practitioners serve as trusted advisors to our clients, combining strategic thinking with deep industry knowledge to solve complex business problems in a team-based environment. We architect operating models and processes that enable growth, optimize capital, and maximize operational efficiency. We implement innovative technology solutions spanning core, digital, data, analytics, cloud and AI.

Deloitte's Financial Services Industry consulting practice is the largest in the world, serving over 90% of Fortune 500 banking, insurance, securities, investment management, and real estate companies.

Qualifications

Required:

• Bachelor's degree in Computer Science, Engineering, or Information Systems
• 8+ years of Guidewire implementation experience, including 2+ full-lifecycle deployments of PolicyCenter, BillingCenter, and/or ClaimCenter in production
• 5+ years of Guidewire configuration and integration experience using Gosu and Java, including rules, screens, workflows, batch processes, and plugins
• 3+ years of experience leading Guidewire integration patterns using application programming interfaces, events, messaging, and web services with rating, customer relationship management, data, and document management systems
• 2+ years of experience with Guidewire Cloud or Guidewire upgrades, including development operations pipelines, environment management, and release governance
• Ability to travel 50-75%, on average, based on the work you do and the clients and industries/sectors you serve.
• Must be legally authorized to work in the United States without the need for employer sponsorship, now or at any time in the future.

Preferred:

• Guidewire certifications in PolicyCenter, BillingCenter, ClaimCenter, Integration, and/or Cloud
• Experience with cloud and development operations tools used for Guidewire, including Amazon Web Services or Microsoft Azure, Kubernetes, Terraform, GitHub Actions, Azure DevOps, Jenkins, SonarQube, and observability platforms
• Experience with Guidewire DataHub/InfoCenter, data migration tools, and analytics pipelines for underwriting, billing, and/or claims
• Experience implementing Insurance Services Office or bureau content, rating engines, and product model design for personal and/or commercial lines
• Experience with Guidewire performance engineering, including load testing, tuning, caching, and database optimization
• Experience leading global delivery teams and Agile delivery frameworks, including Scrum, Kanban, and/or Scaled Agile Framework

The wage range for this role takes into account the wide range of factors that are considered in making compensation decisions including but not limited to skill sets; experience and training; licensure and certifications; and other business and organizational needs. The disclosed range estimate has not been adjusted for the applicable geographic differential associated with the location at which the position may be filled. At Deloitte, it is not typical for an individual to be hired at or near the top of the range for their role and compensation decisions are dependent on the facts and circumstances of each case. A reasonable estimate of the current range is $180,200 to $355,100.

You may also be eligible to participate in a discretionary annual incentive program, subject to the rules governing the program, whereby an award, if any, depends on various factors, including, without limitation, individual and organizational performance.