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Senior Supervisory Attorney – Complex Claim Unit

American Family Insurance · Madison, WI · $113,000–$194,000 a year · Full time

Posted Sep 29, 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 case where you had to change strategy midway because the facts shifted.

What they are checking: Whether they adjust the plan as litigation unfolds instead of sticking to the first theory.

How do you keep a large caseload of complex files organized so none of them slip?

What they are checking: Whether they have a reliable system for deadlines, reserves and reporting across many files.

Tell me about the toughest complex litigation matter you have handled. What was your role in the outcome?

What they are checking: Whether they have real experience with high-exposure cases and can explain their own judgment calls.

What would you do

How do you hold outside counsel accountable when they miss deadlines or drift from the litigation guidelines?

What they are checking: Whether they actively manage panel counsel instead of letting the firm run the file.

Outside counsel sends a large bill with block billing and work you did not approve. What do you do?

What they are checking: Whether they manage legal spend firmly while keeping a working relationship with the firm.

A claims partner asks you for quick legal advice on a gray-area issue. How do you respond?

What they are checking: Whether they give practical, timely advice while flagging real risk clearly.

How do you report case status and exposure to non-lawyer leaders who need a clear answer?

What they are checking: Whether they can explain legal risk in plain terms that support reserve and business decisions.

About the work

Walk me through how you build a defense strategy on a new complex file in the first 30 days.

What they are checking: Whether they front-load analysis of liability, damages and coverage so the file has a plan from day one.

What goes into a well-drafted Reservation of Rights letter, and where do they usually go wrong?

What they are checking: Whether they know Wisconsin coverage law well enough to protect the company without waiving defenses.

How do you decide when a case should settle rather than go to trial?

What they are checking: Whether they weigh verdict risk, cost of defense and the insured's interests with clear judgment.

How do you handle a case where the insured's interests and the company's interests start to diverge?

What they are checking: Whether they understand the tripartite relationship and their ethical duties in it.

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The full job description

As published by American Family Insurance.

You will provide effective legal representation by retaining and supervising outside counsel that handles complex litigation involving either the corporation and/or its insureds within established corporate guidelines and the applicable code of professional responsibility. Perform basic initial coverage review and draft Reservation of Rights letters on certain files. You may also provide legal advice to our business partners on an as needed basis. You will report to the Senior Manager, Legal. Internal candidates are encouraged to apply regardless of location and will be considered based upon the needs of the role. #LI-remote Position Compensation Range: $113,000.00 - $194,000.00 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 Manage caseload to obtain successful outcomes through: • • Proactively managing Outside Counsel. • Holding outside counsel accountable for meeting the requirements of the Company. • Implementing appropriate strategy to drive the file toward successful resolution. • Specific analysis and development of defense strategy for the life cycle of the file, to include initial file analysis and strategy, and following through on the strategy of a file and adjusting same as the litigation dictates. • Adherence to litigation best practices (i.e. develop strategy, appropriate motion practice, proper trial preparations, etc.) • Timely escalation and reporting on files as required. • Collaboratively participate in regular meetings/communications with management and attorney team members to review file handling/strategy, reserving practices, risk management, process adherence, and performance • Effective presentation of files to senior leadership. • Actively manage file cycle, including timely file closing. • Implementing appropriate reserving practices, including early recognition of reserve deficiencies, timely adjustments, and obtaining authority when appropriate. • Early recognition of coverage issues, drafting RORs, and incorporating coverage analysis or status into case evaluations and engage Coverage partners as appropriate. Specialized Knowledge & Skills Requirements • Demonstrated experience providing customer-driven solutions, support or service • Demonstrated experience preparing civil pleadings, motions and discovery and deposing witnesses. • Demonstrated litigation experience. • Solid knowledge and understanding of rules of Professional Responsibility for the jurisdiction in which they practice. • Solid knowledge and understanding of tort, contract, and insurance law. • Admitted to the state bar in the state where they are located or (1) admission to the bar within one year of hire for individuals who must pass a bar exam or portions of a bar exam to be admitted or (2) bar admission as soon as practicable but no later than 60 days of hire for individuals with diploma privilege or who are eligible for in-house counsel registration. • Juris Doctor Additional Specialized Knowledge & Skills • Prior experience with external counsel management a plus. • Experience with first- and third-party bad faith litigation in western U.S. states a plus. • Must take and pass an adjuster license exam within 6 months of hire. Travel Requirements • Up to 50%. Physical Requirements • Work that primarily involves sitting/standing. 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. #LI-MN2

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