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Lead Guidewire Developer (Hybrid)

American Family Insurance · Madison, WI · $131,000–$220,000 a year · Full time

Posted Sep 25, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you mentored a developer who was struggling. What changed?

What they are checking: Whether they build up the team, which the posting names as a core part of the lead role.

Tell me about a technical decision you made that turned out wrong. How did you handle it?

What they are checking: Whether they own mistakes openly and correct course as a leader.

What would you do

How do you run a technical design review so it catches problems without slowing the team down?

What they are checking: Whether they can lead design decisions that balance quality and delivery speed.

A production issue is blocking agents from issuing commercial policies. How do you lead the response?

What they are checking: Whether they stay calm, find the cause and communicate well when the business is stuck.

A business stakeholder wants a change that you think will hurt the platform long term. How do you handle it?

What they are checking: Whether they can push back with clear tradeoffs and offer a better path.

About the work

Tell me about your experience with Guidewire PolicyCenter, especially commercial lines. What parts of the product model have you configured?

What they are checking: Whether they have real depth in PolicyCenter for commercial lines, which is more complex than personal lines.

How do you decide between configuration and custom Gosu code when solving a business need?

What they are checking: Whether they protect upgrade paths by keeping customization only where it is truly needed.

Walk me through how you would plan a move of PolicyCenter to Guidewire Cloud.

What they are checking: Whether they understand cloud standards and the work of removing old customizations.

How do you integrate PolicyCenter with rating, billing or other systems in a way that stays maintainable?

What they are checking: Whether they design clean integrations instead of fragile point-to-point links.

What modern engineering practices have you brought to a Guidewire team, like automated tests or CI/CD?

What they are checking: Whether they can move a legacy-heavy platform toward faster, safer delivery.

How do you build security into Guidewire development?

What they are checking: Whether they think about access, data protection and secure coding in a system holding customer data.

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The full job description

As published by American Family Insurance.

As a Lead Guidewire Developer with American Family Insurance, you will provide technical leadership for the Guidewire Commercial Lines PolicyCenter platform, driving the design, development, modernization, and support of critical business applications. You will collaborate with architects, engineering teams, and business stakeholders to deliver secure, scalable, and maintainable solutions, while influencing technical direction, advancing modern engineering practices, and ensuring operational excellence. Through mentorship, problem solving, and strategic decision-making, you will help build a high-performing platform that supports current business needs and future growth. You will report to Senior Manager Engineering. Relocation assistance may be available. #LI-Hybrid Position Compensation Range: $131,000.00 - $220,000.00 Pay Rate Type: Salary Compensation may vary based on the job level and your geographic work location. Relocation support is offered for eligible candidates. Primary Accountabilities: • Serves as the technical lead for the Guidewire CLPC platform, providing guidance and leadership for complex business and technology solutions. • Leads solution design, technical reviews, and engineering decision-making to ensure scalable, secure, and maintainable application architectures. • Partners with architects, product teams, engineering leaders, and business stakeholders to align technical solutions with business objectives. • Drives platform reliability, resiliency, performance, maintainability, and operational excellence. • Leads root cause analysis and resolution of complex production issues and implements long-term corrective actions. • Identifies and drives opportunities to reduce technical debt and improve overall platform health and supportability. • Establishes and promotes engineering standards, development best practices, and quality expectations across the platform. • Provides technical leadership, mentoring, and coaching to engineers through design reviews, knowledge sharing, and guidance on technical solutions. • Evaluates emerging technologies and engineering capabilities, including automation and AI-assisted development opportunities, to improve engineering effectiveness. • Leads and influences platform modernization initiatives focused on scalability, resiliency, maintainability, automation, and long-term sustainability. • Collaborates across teams to understand system dependencies, integration requirements, risks, and technology impacts. • Supports estimation, planning, and technical execution activities for complex initiatives and platform enhancements. Specialized Knowledge & Skills Requirements: • Demonstrated experience providing customer-driven solutions, support, or service. • Demonstrated experience analyzing and understanding complex software systems. • Demonstrated experience communicating technical information. • Demonstrated experience developing different solution-delivery and design approaches and solutions to customers. • Demonstrated experience developing different solution-delivery and design approaches and solutions to customers. • Demonstrated experience developing complex software/systems using one or more programming language. • Demonstrated experience analyzing and estimating project size and work efforts for software solutions. • Demonstrated experience providing technical guidance and leadership to less experienced staff. • Extensive knowledge and understanding of software development and design standards and methodologies. • Extensive knowledge and understanding of infrastructure technologies, operating systems, and the interconnectivity between infrastructure platforms and software tools. • Extensive knowledge and understanding of systems development life cycle (SDLC). • Solid knowledge and understanding of application architecture and design alternatives. • Solid Knowledge and understanding of integration and migration strategies and technologies. Preferred Qualifications: • Experience in software engineering, application development, or platform engineering supporting complex enterprise applications. • Experience with Guidewire PolicyCenter in development, solution design, support, or technical leadership roles strongly preferred. • Knowledge of Guidewire BillingCenter, ClaimCenter, integrations, and modernization initiatives. • Experience supporting business-critical applications requiring high availability, reliability, and operational excellence. • Strong analytical, troubleshooting, problem-solving, and decision-making skills. • Demonstrated ability to influence technical direction and collaborate effectively across architecture, engineering, product, and business teams. • Experience leading technical design discussions, architecture reviews, and solution planning efforts. • Experience improving application performance, resiliency, reliability, and operational effectiveness. • Experience performing root cause analysis and resolving complex production issues. • Familiarity with cloud technologies, automation, observability tools, and modern engineering practices. • Interest in emerging technologies, including AI-assisted engineering and intelligent automation. Licenses: Not Applicable. Travel Requirements Up to 10%. Physical Requirement s Work that primarily involves sitting/standing. Working Conditions Not Applicable. Additional Information • To ensure a strong start, all employees participate in our New Employee Orientation during their first week.  This experience is held in person at our Madison, WI Headquarters or one of our AmFam core locations to help you connect with our mission, meet key team members and build relationships that support your growth.  At times, sessions may be delivered virtually based on scheduling and availability. • Offer to selected candidate will be made contingent on the results of applicable background checks • Offer to selected candidate is contingent on signing a non-disclosure agreement for proprietary information, trade secrets, and inventions • Sponsorship will not be considered for this position unless specified in the posting In this hybrid role, you will be expected to work a minimum of 10 days per month out of our Madison, WI or Boston, MA offices. We provide benefits that support your physical, emotional, and financial wellbeing. You will have access to comprehensive medical, dental, vision and wellbeing benefits that enable you to take care of your health. We also offer a competitive 401(k) contribution, a pension plan, an annual incentive, 9 paid holidays and a paid time off program (23 days accrued annually for full-time employees). In addition, our student loan repayment program and paid-family leave are available to support our employees and their families. Interns and contingent workers are not eligible for American Family Insurance Group benefits. We are an equal opportunity employer. It is our policy to comply with all applicable federal, state and local laws pertaining to non-discrimination, non-harassment and equal opportunity. We also consider qualified applicants with criminal histories, consistent with applicable federal, state and local law. American Family Insurance is committed to the full inclusion of all qualified individuals. If a reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or to receive other benefits and privileges of employment, please email AskHR@AmFam.com to request a reasonable accommodation. #LI-AB1

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