JobsAmerican Family Insurance

Lead Application Development Engineer (Hybrid)

American Family Insurance · Madison, WI

Posted Aug 27, 2026 · We last checked this listing on Sep 20, 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.

Behavioral

Walk me through a time you had to design a solution architecture for a complex system with a lot of moving dependencies. How did you approach it?

whether the candidate can structure and communicate architectural decision-making, not just execute given designs

Tell me about a time you mentored a less experienced engineer through a technical problem they were stuck on.

actual mentoring style and whether they build capability in others rather than just fixing things themselves

Describe a situation where you had to explain a technical tradeoff to a non-technical stakeholder who disagreed with your recommendation.

communication skill and ability to influence without authority

Tell me about a time you had to estimate scope and timeline for a project with a lot of unknowns. How close did you get, and what did you miss?

honesty and rigor in estimation, a core responsibility called out in the posting

What does a strong code review culture look like to you, and how have you built or improved one on a team?

whether they actually champion quality practices or just say they value them

Technical

Tell me about a Java-based service you built or led that used Spring Boot and had to scale. What were the tradeoffs you made?

depth of real hands-on Java and Spring Boot experience versus surface familiarity

How would you design a RESTful API for a system that needs to integrate with both legacy mainframe data and a newer microservice?

practical grasp of API-first design and comfort bridging legacy and modern systems

How have you used AI tools like Claude or similar in code review or troubleshooting, and what did you learn about where they help or fall short?

genuine hands-on exposure to AI-assisted development versus buzzword familiarity

What's your experience working with DB2 or NoSQL databases, and how did you decide which fit a given use case?

real database design judgment versus just checking a box on a resume

How do you approach breaking a monolithic legacy application into services without disrupting the business that depends on it?

depth of thinking on modernization strategy, a central theme of this role

Have you worked in insurance or another regulated industry, and if so, how did that shape the way you approached system design or data handling?

awareness of compliance and risk considerations relevant to insurance data

Situational

Suppose you're leading a migration of a legacy application to a modern cloud environment and midway through, the team discovers a critical dependency wasn't documented. What do you do?

how the candidate handles risk discovery and replanning under pressure during a migration

If a production issue came in on a service you architected and the root cause pointed to a design decision you made, how would you handle it with your team and leadership?

accountability and composure when their own design choices are the source of a problem

Imagine two senior engineers on your team disagree strongly on an architectural approach and it's slowing down delivery. How do you resolve it?

leadership style in technical conflict, since this role sits between hands-on coding and team leadership

Practice this interview out loud.

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The full job description

As published by American Family Insurance.

Join American Family Insurance as a Lead Applications Development Engineer and play a pivotal role in shaping the future of our technology landscape. In this role, you'll provide technical vision and leadership while remaining hands-on with Java development and RESTful API development architecting scalable solutions that deliver meaningful business impact. You'll have the opportunity to help drive the team's evolution by leveraging emerging technologies such as Claude AI and cloud-native platforms, modernizing legacy applications, and leading critical system migrations to modern data center and cloud environments. Beyond building innovative solutions, you'll guide and mentor teammates, introduce new ways of working, and champion best practices that enhance the team's effectiveness, efficiency, and long-term success. Collaborating across teams, you'll help create high-quality software that powers exceptional experiences for our customers and the business. You will report to the Engineering Delivery Manager. Role not eligible for sponsorship. #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. Key Responsibilities Drive Technical Strategy and Solution Design • Serve as a trusted technical expert during project planning, helping define resource needs, required skills, timelines, tools, and technologies. • Evaluate and contribute to proof-of-concept initiatives that validate innovative solutions and reduce project risk. • Translate business goals, requirements, and use cases into scalable technical designs and actionable development plans. Architect High-Quality Solutions • Analyze complex system requirements and design robust, efficient, and maintainable solutions. • Identify and manage system dependencies, ensuring seamless integration across platforms and applications. • Partner with stakeholders and technical teams to validate architectural decisions and drive best practices. Solve Complex Technical Challenges • Provide advanced Java coding expertise and hands-on support for high-risk features, critical initiatives, and complex technical issues. • Guide teams through architectural and development challenges by recommending effective solutions and implementation strategies. Champion Quality and Continuous Improvement • Lead and participate in testing activities, including unit testing and system integration testing, to ensure high-quality deliverables. • Facilitate development reviews, walkthroughs, and knowledge-sharing sessions that strengthen team capabilities. • Mentor team members by sharing technical expertise, best practices, and problem-solving approaches. Promote Collaboration and Operational Excellence • Collaborate with cross-functional partners to optimize system workflows, data utilization, and business processes. • Document design decisions, estimates, technical assumptions, code modules, and performance metrics to maintain organizational standards and support future scalability. • Ensure technology solutions align with business objectives while improving efficiency, reliability, and user experience. What Success Looks Like • You are a technical leader who bridges business needs and technology solutions, influences key design decisions, solves complex challenges, and empowers teams to deliver scalable, high-performing systems that drive organizational success. • You have the opportunity to help the team grow in utilization of Claude for coding reviews and analysis as well as cloud technologies. Specialized Knowledge & Skills Requirements • Demonstrated experience analyzing and understanding complex software and systems. • Demonstrated experience communicating technical information to technical and non-technical audiences. • Demonstrated experience developing and delivering multiple solution design approaches to meet customer needs. • Demonstrated experience developing complex software and systems using one or more programming languages. • Demonstrated experience analyzing requirements and estimating project size, scope, and work effort for software solutions. • Demonstrated experience providing technical guidance, mentorship, and leadership to less experienced staff. • Extensive knowledge and understanding of RESTful software development standards, methodologies, and best practices. • Extensive knowledge and understanding of infrastructure technologies, operating systems, and the interconnectivity between infrastructure platforms and software tools. • Extensive knowledge and understanding of the Systems Development Life Cycle (SDLC). • Solid knowledge and understanding of application architecture principles and design alternatives.   Preferred Qualifications: • Bachelor’s degree in computer science, Information Technology, Engineering, or a related field • Extensive experience in application development with strong proficiency coding, analysis and design in Java and modern Java-based frameworks such as Spring Boot and Spring • Experience using Claude - code reviews, analysis and troubleshooting. • Demonstrated experience leading technical design, development, and implementation efforts across complex software solutions • Experience building and supporting API-First(RESTful and SOAP) services, and service-oriented or microservices-based application architectures • Familiarity with cloud-enabled technologies and platforms such as AWS, Azure, or Google Cloud Platform • Familiarity with DevOps practices and tools supporting continuous integration and continuous delivery • Knowledge of containerization and orchestration technologies such as Docker and Kubernetes • Strong understanding of software engineering best practices, including object-oriented design, design patterns, code reviews, and automated testing • Experience working with DB2 and NoSQL databases • Ability to troubleshoot and resolve complex technical issues in development, test, and production environments • Experience mentoring engineers, providing technical guidance, and supporting team development • Strong collaboration and communication skills with the ability to partner effectively across engineering, product, architecture, and business teams • Experience working in Agile environments and contributing to iterative delivery practices • Experience in the insurance, financial services, or other highly regulated industry is preferred • Passion for delivering scalable, secure, and reliable technology solutions that improve customer and business outcomes. Licenses: •Not Applicable. Travel Requirements •Up to 10%. Physical Requirements •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 either the 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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