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Personal Insurance Consultant Supervisor

Job in Milwaukee, Milwaukee County, Wisconsin, 53244, USA
Listing for: WEA Member Benefits
Full Time position
Listed on 2026-02-12
Job specializations:
  • Insurance
Salary/Wage Range or Industry Benchmark: 60000 - 80000 USD Yearly USD 60000.00 80000.00 YEAR
Job Description & How to Apply Below

Personal Insurance Consultant Supervisor

Home » Personal Insurance Consultant Supervisor

Join Our Team:
Supervisor, Home and Auto Personal Insurance Lines

Are you a motivated leader with a passion for developing teams and driving results? We’re looking for a dynamic supervisor for our home and auto insurance lines to join a growing and dedicated team that serves Wisconsin public school employees and their families.

At WEA Member Benefits, we are dedicated to serving our members with highly rated retirement savings, financial planning, and personal insurance programs for public school employees. Our employees have a passion for our mission and vision and strive to deliver “A+ Performance” in everything we do. WEA Member Benefits was created by Wisconsin educators for Wisconsin educators over 50 years ago.

Our culture, work environment, and team have made our organization a 6-time “Best Places To Work” winner (Madison Magazine) and 3-time Top Workplaces winner (Wisconsin State Journal).

Why work with us?
  • Competitive Salary and Performance Bonuses: Achieve sales targets and contribute to a growing team while earning generous performance-based incentives.
  • Unmatched 401(k) Benefits: Subject to the terms and eligibility requirements of the applicable 401(k) plan, the Company will contribute an amount equal to twenty-five percent (25%) of your annual base salary to your 401(k) account. This contribution is a non‑matching employer contribution and does not require any employee contribution.
  • Exceptional Work Culture: We are committed to fostering personal and professional growth with a positive, supportive work environment that encourages collaboration and innovation.
  • Comprehensive Benefits Package: Includes health, dental, vision, paid time off, and more to ensure you and your family are taken care of.
  • Meaningful Work: You’ll play a key role in supporting Wisconsin’s public education community by providing essential financial services to employees and their families.
Key responsibilities
  • Lead the charge in achieving personal insurance sales goals, ensuring that both new and existing members are fully informed about our products and services.
  • Consult with potential members to assess their personal insurance needs and offer tailored recommendations.
  • Expand the program by identifying new opportunities for growth, leveraging cross‑selling techniques, referrals, and additional lead generation strategies to boost sales.

Team Development and Management

  • Supervise and mentor a team of 4‑5 Personal Insurance Consultants (PICs), ensuring their continuous development and success in reaching sales targets.
  • Provide guidance and support, actively listening to employees to understand their individual strengths, challenges, and goals.
  • Cultivate a positive and motivating work environment by offering regular feedback, resolving conflicts, and driving employee engagement.
  • Oversee team performance and ensure the highest level of customer service.
  • Assist in managing operational expenditures, ensuring alignment with budget goals and financial targets.
  • Implement changes to products, marketing, services, and systems as needed to meet evolving member needs.
  • Monitor and support cross‑selling initiatives and the implementation of company‑wide lead generation programs.
  • Provide necessary training to staff to ensure compliance with company policies, underwriting standards, and new business processes.
Required experience and skills
  • Education: A Bachelor’s degree in Business, Marketing, Sales, or a related field, or commensurate experience.
  • Experience: Minimum of 2‑3 years of experience in insurance sales, sales leadership, or a related field in the financial services industry.
  • Licensing: Must hold or be able to obtain a Wisconsin Property and Casualty License within six months of hire.
  • Leadership

    Skills:

    Proven ability to lead and motivate a team, foster a collaborative environment, and drive results.
  • Communication

    Skills:

    Excellent verbal and written communication skills, with the ability to effectively explain complex insurance products and services to a variety of audiences.
  • Problem‑Solving: Strong decision‑making abilities with a proactive approach to…
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