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Senior Java Engineer (Hybrid)

American Family Insurance · Madison, WI · $99,000–$167,000 a year · Full time

Posted Jun 16, 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

Walk me through a system you built or maintained that sat on the critical path for a transaction, something where an outage or a bug would have hit customers directly. How did you design it to fail safely?

What they are checking: whether the candidate has real experience with high-stakes, always-on systems and thinks about failure modes, not just happy-path features

Give me an example of taking a high-level business requirement or use case and turning it into a low-level technical design. What did that document or design plan actually include?

What they are checking: whether they can genuinely translate business needs into engineering specs, a core accountability listed in the posting

Tell me about a time you had to estimate the size or effort of a software project and you got it wrong. What happened and what did you change afterward?

What they are checking: honesty and growth around estimation skills, which the posting explicitly calls out

Tell me about a code or design walkthrough you led. How did you handle pushback from someone more senior, or from someone who clearly didn't understand the design?

What they are checking: communication skill and technical leadership under disagreement, since the role includes leading walkthroughs and providing technical guidance

Tell me about a time a stakeholder, maybe a product owner or someone on the business side, asked for something you knew was technically risky or wrong. How did you handle that conversation?

What they are checking: customer-driven service orientation and ability to push back constructively, both called out in the posting

What would you do

Say you inherit a rating or eligibility service with almost no documentation and you need to change its behavior without breaking downstream sales platforms. How do you approach figuring out what's safe to touch?

What they are checking: ability to reverse-engineer legacy systems and manage risk in a system they don't fully understand yet

Picture a scenario where a change to a shared product data service needs to go out, but three other teams downstream depend on that data and none of them were part of the design conversation. What do you do before you ship it?

What they are checking: stakeholder awareness and communication discipline in a platform-team context where changes ripple outward

Imagine you find a performance or security issue in a service that's currently live and processing policy transactions. It's not on fire yet, but it will be soon. Walk me through what you'd do in the first day and over the following week.

What they are checking: judgment on prioritization and risk management in a system where downtime has real business consequences

About the work

Tell me about your experience building Spring Boot RESTful APIs on AWS. What does a typical service architecture look like for you, from the API layer down to the data store?

What they are checking: depth of hands-on Java/Spring Boot/AWS experience versus surface familiarity

How have you used AI coding tools like Copilot or Claude Code in your day-to-day development? Where do you trust them and where do you not?

What they are checking: real, specific usage of AI tools versus a vague claim of proficiency

What's your experience with SQL and data modeling in the context of insurance products or policy data? Have you worked with anything like rate tables or eligibility rules engines?

What they are checking: whether the insurance-domain knowledge and SQL skill are real or just listed

How do you approach integrating a new service with existing applications and databases, especially when the integration technology is something the rest of your team hasn't used before?

What they are checking: depth on integration and migration strategy, which the posting names as a required skill area

What testing do you personally write versus what you rely on the team or automation to catch, on a service like this one where correctness really matters?

What they are checking: whether their sense of testing responsibility matches the rigor a critical-path financial system actually needs

Practice this interview out loud.

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The full job description

As published by American Family Insurance.

The Senior Java Engineer collaborates with others in the division to provide and maintain applications that meet business needs. You will be responsible for software design and development for moderate to complex business solutions, providing technical guidance and leadership for specific applications. You will be on a team that owns core platform services for insurance rating, eligibility, and product data systems that power AmFam's sales platforms and internal rate engines. You will also be a direct contributor to the value delivered by our commercial platform. The services you will maintain are on the critical path for every policy transaction that flows through the platforms we support. You will report to the Senior Manager, Engineering. In this flex office/home role, you will be expected to work a minimum of 10 days per month from one either Madison, WI 53783 or Boston, MA 02110 Internal candidates are encouraged to apply and should review the internal mobility guidelines in the hybrid policy reference guide for more information on potential relocation. Depending on the candidate pool, this position may be filled at a lower level to maintain alignment with experience and qualifications. We will not consider candidates who require current or future sponsorship for this position Position Compensation Range: $99,000.00 - $167,000.00 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 • You will analyze high level system specifications, system requirements and/or use cases. • You will convert information into low level specifications and system design plan. • You will understand and identify system dependencies. • You will provide appropriate documentation for design decisions, estimating assumptions, code modules, and performance metrics as required by organization standards. • You will define, conduct, and/or participate in testing (i.e. unit, system integration). • You will prepare, lead and/or participate in development walkthroughs. • You will collaborate with others regarding effectiveness of systems flow, data usage and manual or automated processes to verify requirements. • You will ensure software development meets standards for programming, design, performance, quality, and security. Identifies and recommends areas for improvement in planning, design, development, and testing. Specialized Knowledge & Skills Requirement • Demonstrated experience providing customer-driven solutions, support or service. • Basic knowledge and understanding of application architecture, design alternatives, and development standards. • Demonstrated experience communicating technical information. • Demonstrated experience developing complex software/systems using one or more programming language. • Demonstrated experience establishing, using and supporting integration and communications technologies between applications, databases and technology platforms. • Demonstrated experience analyzing and estimating project size and work efforts for software solutions. • Demonstrated experience writing and modeling application system design and program specifications. • Solid knowledge and understanding of systems development life cycle (SDLC). • Solid Knowledge and understanding of integration and migration strategies and technologies. • Travel requirements up to 10%. 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 Additional Qualifications • 5+ years AWS-backed Java software development experience building out Spring Boot, Restful API aps, Python, SQL… • AI proficiency with tools such as MS Copilot, Claude Code… • Insurance industry experience #LI-Hybrid 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.

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