JobsAmerican Family Insurance

Lead Application Development Engineer – Payment Technology

American Family Insurance · Madison, WI

Posted Aug 30, 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

Tell me about a time you had to give technical direction that a more senior architect or a business stakeholder disagreed with. How did that play out?

whether they can hold a technical line under pressure without becoming rigid or losing the relationship

Describe how you've set or enforced an engineering standard, for example around observability, testing, or security, on a team that wasn't doing it consistently before. What resistance did you hit?

whether they can actually change team behavior, not just personally follow best practices

Tell me about a time you mentored an engineer who was struggling with a complex system. What did you do differently for them versus a stronger engineer on the team?

real mentoring instinct and adaptability, not a generic answer about being available

Tell me about a design decision you made that you later had to reverse. What did you miss the first time?

intellectual honesty and whether they learn from architectural mistakes rather than defend them

Technical

Tell me about a legacy application you moved to a cloud-native architecture. What made you choose the pattern you chose, and what broke along the way that you didn't expect?

real hands-on experience with modernization, not just familiarity with the vocabulary

Walk me through how you'd design a payment processing capability that needs to be both event-driven and strongly consistent for money movement. Where do you accept eventual consistency and where do you refuse to?

whether the candidate understands the specific tradeoffs of distributed systems in a domain where money can't just eventually reconcile

What AWS services have you actually used to run a production payment or transactional workload, and what went wrong with one of them that taught you something?

depth versus resume-keyword familiarity with the cloud stack

How have you used AI-assisted tools or cloud AI services in your engineering work, and where did you decide not to trust the output?

genuine, current use of AI tooling with judgment about its limits, not just a claim of adoption

How do you estimate the size and effort of a complex piece of work when the requirements are still fuzzy, and how do you communicate that uncertainty to the business side?

maturity in estimation and honest communication versus false confidence

Situational

Say you're handed a monolithic, high-volume transactional payment application that the business wants moved to microservices in the next year. How do you decide what to break apart first and what stays put?

practical judgment about migration sequencing versus a textbook big-bang rewrite instinct

A high-risk payment integration is failing intermittently in production and the root cause isn't obvious. Walk me through how you'd approach diagnosing it without taking the whole system down further.

production troubleshooting discipline under pressure with a bias toward containment

If product wants a new payment feature shipped fast, and you know the underlying integration has fragile dependencies, how do you balance speed with not building on top of a mess?

how they negotiate delivery pressure against technical debt in a regulated, money-touching system

Practice this interview out loud.

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The full job description

As published by American Family Insurance.

Join American Family Insurance’s Payment Technology team as a Lead Application Development Engineer [TB2.1]and help modernize the secure, scalable applications that power payment experiences across the enterprise. Reporting to the Senior Manager, you will combine hands-on engineering with technical leadership to move legacy solutions to cloud-native architectures and improve customer and business outcomes. You will partner with product, engineering, architecture, and business teams to design and deliver resilient payment capabilities for American Family Insurance. In this role, you will guide technical decisions, mentor engineers, and apply cloud and AI-enabled practices to strengthen quality, speed, and reliability. 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. This role does not have approval for sponsorship now or in the futire. This includes H1 transfers, OPT, CPT, F1 Visa and STEM. Primary Accountabilities - What You’ll Lead • Own the technical direction for secure, scalable payment applications—from early concepts and architecture through implementation and production. • Shape the future of our payment platform by modernizing legacy solutions with cloud-native, microservices, API, event-driven, and distributed-system patterns. • Turn coplex needs into practical solutions by partnering with product, architecture, engineering, and business teams to define designs and delivery plans. • Stay close to the code , leading development for complex or high-risk capabilities and solving challenges across integrations and dependencies. • Set the standard for engineering excellence across design, testing, security, observability, performance, documentation, and production readiness. • Grow the team’s technical capabilities by mentoring engineers, guiding key decisions, and connecting the work to meaningful customer and business outcomes. 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 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 We value skills gained through many paths. If you meet most of these qualifications and are excited about payment technology , we encourage you to apply. • Bachelor’s degree in a relevant field or equivalent practical experience. • Approximately 10+ years in software engineering, application development, or enterprise solution delivery, including 7+ years with Java, Spring Boot, or comparable backend technologies. • 5+ years building and deploying cloud-native applications, ideally on AWS, using microservices, REST APIs, event-driven architecture, and distributed systems. • Experience modernizing legacy or high-volume transactional applications; payment-platform, financial-services, or similarly regulated-industry experience is helpful but not required. • Experience with relevant AWS services, containers, CI/CD, Infrastructure as Code, automated testing, observability, security, and resilient production operations. • Ability to turn business needs into scalable technical designs and use approved AI-assisted tools or cloud AI services to improve engineering quality and efficiency. • Demonstrated technical leadership through mentoring, architecture and code reviews, stakeholder influence, and delivery of customer-focused business outcomes. In this HYBRID role, you will work 10 days per month from one of the following office locations: Madison, WI 53783; Boston, MA 02110 Internal candidates are encouraged to apply regardless of location and will be considered based on the needs of the role. Licenses • Not Applicable. Travel Requirements • Up to 10% travel required. Physical Requirements • Work primarily involves sitting and standing for extended periods. 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 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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