JobsAmerican Family Insurance

Sales District Leader - South Milwaukee, WI (Primarily Field)

American Family Insurance · Milwaukee, WI

Posted Sep 10, 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 influence someone's business decisions when you had no direct authority over them.

real track record of persuasion versus command-and-control management habits

Describe a time you built a business plan with a partner who ultimately controlled whether to follow it or not.

comfort operating in a consultative rather than directive role

Tell me about a time you had to prioritize between what corporate wanted and what a local partner or client needed.

ability to balance corporate strategy with field-level realities

Tell me about a time you had to deliver hard feedback to someone you couldn't fire or formally discipline.

skill in managing performance without traditional employer leverage

Why are you interested in this kind of coaching and recruiting role rather than a traditional sales management job with direct reports?

genuine motivation and fit with the unique employee-managing-contractors structure

Technical

How do you go about recruiting someone to become a captive agent, and what do you look for in a candidate you'd want to build an agency?

concrete recruiting process and judgment on agent selection criteria

What does a district profit and growth plan look like to you, and what numbers would you actually track month to month?

fluency with financial analysis and reporting expected in the role

What's your experience with agency operations or leading people in the insurance field specifically?

whether candidate has direct insurance agency or captive-agent experience versus general sales management

How would you help an agency owner understand and use business systems or data tools they aren't currently leveraging well?

ability to translate corporate systems into practical value for independent business owners

Describe how you've managed a budget or resource allocation across multiple teams or locations before.

budget management competency named in the requirements

Situational

Walk me through how you would coach an agency owner who is struggling with growth, given that you can't just tell them what to do like an employee.

understanding of the independent contractor relationship and influence-without-authority coaching style

If an agency owner is hitting their sales numbers but running the office in a way that creates compliance or reputational risk, what do you do?

balancing respect for owner autonomy against corporate risk management

You're spending most of your week in the field visiting agencies across the district. How do you decide which agencies get your time on a given week?

time management and prioritization skill in a field-heavy role

An agency owner tells you they don't want to follow the state sales plan because it doesn't fit their market. How do you respond?

conflict resolution style and respect for owner control while still driving results

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The full job description

As published by American Family Insurance.

You will support the agency business owners in their role as independent contractors who have the right of control over the manner and means by which they sell insurance and otherwise operate their businesses. Coach and advise agency business owners on building the district's profit and growth plan. Key focus areas will be field recruiting agency owners to be captive agents and influencing performance results for those independent contractors. You will report to the Wisconsin State Director. You will be asked to reside in the district (an ideal target would be Milwaukee, WI and surrounding). In this primarily field-based role, you will spend 70% of your time (3-4 days per week) working in the field, directly working with customers, Agents, Agency Staff. On occasion you may be asked to travel to an office location for in person engagement activities such as team meetings, trainings, and culture events. 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 • Support and uphold the role of agency business owners as independent business owners. Ensure that agency business owners understand and make the connection between the corporate strategy and their practices and results; consider both corporate and agency needs when determining priorities. • Provide guidance to agency business owners and staff by exhibiting influence and expertise. Coach and advise agency business owners on sales results and execution of the state sales plan. • Assist agency business owners in understanding the profit of the district, while preserving the agency business owners' right to control the manner and means by which they sell insurance and otherwise run their own businesses. • Manage company programs for the district as they pertain to individual independent agency business owners. • Assist agency business owners as independent contractors in targeting and prioritizing the best sales activities and opportunities for them in their market and individual situation. • Provide business expertise to agency business owners to assist them in ensuring the successful operation of their businesses. • Sources and selects agency business owners to fill openings. • Build relationship with agency business owners and staff, respecting their role as owners of their own businesses. Specialized Knowledge & Skills Requirements • Demonstrated experience providing customer-driven solutions, support and service. • Basic knowledge and understanding of business systems and how to leverage them to gain efficiencies in a business environment. • Prior management experience or demonstrated experience leading project teams. • Solid knowledge of project management methodologies, practices, techniques and tools. • Solid knowledge and understanding of financial analysis and reporting. • Prior experience developing and executing operational business plans and marketing plans. • Solid knowledge and understanding of budget management concepts. Preferred Knowledge & Skills • Previous agency experience or experience leading or influencing agency owners in the field. • You will be asked to reside in the district (an ideal target would be Milwaukee, WI and surrounding). Licenses • Required by state statutes to have proper insurance licensing to sell, solicit or negotiate insurance products: Property and Casualty (personal lines authority does not qualify), Life, and Health. • Valid driver's license required plus an acceptable driving record. Travel Requirements • Up to 50%. 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-DB1

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