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Insurance Agent Training Program Jobs in Milwaukee, WI

HealthMarkets, Inc.

Insurance Agent

Milwaukee, WI · On-site

Insurance Agent Insurance Agent Location: Milwaukee, Wisconsin Job Number HM2025-0840 Date posted ... We'll give you access to leads, quoting tools, training resources, and more so you can focus on ...

HealthMarkets, Inc.

Insurance Agent

Milwaukee, WI · On-site

Well give you access to leads, quoting tools, training resources, and more so you can focus on what ... An Independent licensed insurance agent with HealthMarkets is a commission only opportunity.

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All JobsInsurance Agent Training Program JobsInsurance Agent Training Program Jobs in Milwaukee, WI

Insurance Agent Training Program information

See Milwaukee, WI salary details

$24.6K

$64.1K

$119.7K

How much do insurance agent training program jobs pay per year?

As of Sep 15, 2026, the average yearly pay for insurance agent training program in Milwaukee, WI is $64,062.00, according to ZipRecruiter salary data. Most workers in this role earn between $43,800.00 and $75,900.00 per year, depending on experience, location, and employer.

What is an insurance agent training program?

An Insurance Agent Training Program job is a structured program designed to equip aspiring insurance agents with the knowledge, skills, and licensing required to sell insurance policies. Trainees receive guidance on industry regulations, sales techniques, and product offerings while working under experienced mentors. These programs often combine classroom instruction, hands-on experience, and licensing exam preparation. Many employers offer these programs to develop new agents and help them build a successful career in insurance sales.

What can I expect from the daily responsibilities during the insurance agent training program?

During the Insurance Agent Training Program, you can expect a mix of classroom-style instruction, hands-on learning, and shadowing experienced agents to better understand the sales process and client interactions. You'll engage in role-playing exercises, learn about different insurance products, and practice handling customer inquiries or policy applications. It's common to participate in team meetings, review case studies, and receive regular feedback from mentors or trainers. This structured approach not only builds product knowledge and sales techniques but also helps you develop the confidence needed for real-world success as a licensed Insurance Agent.

What are the key skills and qualifications needed to thrive in the insurance agent training program position, and why are they important?

To thrive in an Insurance Agent Training Program, candidates should have strong interpersonal skills, a basic understanding of sales principles, and preferably a high school diploma or equivalent educational background. Familiarity with CRM software, office productivity tools, and the pursuit of licensing exams such as state insurance licenses are important. Exceptional communication, adaptability, and goal-oriented motivation help individuals stand out in this role. These skills are crucial for building client trust, successfully navigating training, and meeting the demands of a dynamic, client-focused industry.

What are the most commonly searched types of Insurance Agent Training Program jobs in Milwaukee, WI?

The most popular types of Insurance Agent Training Program jobs in Milwaukee, WI are:

What are popular job titles related to Insurance Agent Training Program jobs in Milwaukee, WI?

For Insurance Agent Training Program jobs in Milwaukee, WI, the most frequently searched job titles are:

What job categories do people searching Insurance Agent Training Program jobs in Milwaukee, WI look for?

The top searched job categories for Insurance Agent Training Program jobs in Milwaukee, WI are:

Infographic showing various Insurance Agent Training Program job openings in Milwaukee, WI as of September 2026, with employment types broken down into 1% As Needed, 77% Full Time, 21% Part Time, and 1% Contract. Highlights an 84% Physical, 1% Hybrid, and 15% Remote job distribution, with an average salary of $64,062 per year, or $30.8 per hour.

Insurance Agent - Training Provided

Milwaukee, WI • On-site

Wisconsin Region - Modern Woodmen of America
See more jobs at Wisconsin Region - Modern Woodmen of Americaexternal

$63K - $84K/yr

Full-time

Medical, Dental, Vision, Life, Retirement

Posted 14 days ago

Job description

Benefits:
  • 401(k)
  • 401(k) matching
  • Bonus based on performance
  • Company parties
  • Dental insurance
  • Flexible schedule
  • Health insurance
  • Opportunity for advancement
  • Training & development
  • Vision insurance

Are you someone who thrives on competition, teamwork, and achieving excellence? The Wisconsin Region at Modern Woodmen of America is seeking driven professionals who want to build a career as holistic financial planners, individuals passionate about helping others achieve both financial protection and financial growth. Our team is made up of motivated, service-minded leaders dedicated to making a meaningful difference in the lives of our members and communities. If you’re ready to take on new challenges, grow your career, and make a lasting impact, we’d love to connect with you.
At the Wisconsin Region, our representatives are in business for themselves but never by themselves. We take pride in cultivating a collaborative environment where each member has the tools, knowledge, and encouragement to deliver personalized, compassionate, and knowledgeable service to every client. Together, we are building not just successful practices but lasting relationships and stronger communities.
About Modern Woodmen:
Modern Woodmen is about people. Created for our members. Owned and operated by them too. Together, we’re here for each other, for our families and for the communities we love. We are a member-owned fraternal financial services organization. Together with over 700,000 members, we’ve been touching lives and securing futures since 1883. Modern Woodmen's financial strength is anchored in a robust asset base of $17.14 billion. Guided by a prudent investment philosophy, the organization focuses on high-quality, diversified investments with high industry ratings from A.M. Best and KBRA. With a surplus of $2.42 billion and a solvency ratio of 116.41%, Modern Woodmen is committed to ensuring additional protection for its members, affirming its dedication to long-term financial stability.
Meet Our Regional Director:

Danny Frey II is Regional Director for Modern Woodmen of America, where he focuses on helping members and advisors create lasting impact through financial guidance and community involvement. With nearly 19 years in the industry, Danny brings a blend of experience, leadership, and dedication to Modern Woodmen’s mission of making lives better through service and fraternalism. Before joining the organization in 2007, he owned and operated his own bar and grill, which fueled his passion for building relationships and leading with purpose. Outside of work, Danny enjoys supporting his kids’ sports and spending time working on cars.
Role Responsibilities:
  • Member Consultation: Meet with client members to assess their insurance needs and recommend appropriate coverage.
  • Customer Service: Provide exceptional customer service, addressing client inquiries and resolving issues promptly.
  • Networking: Build and maintain a network of client members through referrals, networking events, and community engagement.
  • Training and Development: Participate in ongoing training and professional development to stay current with industry changes and enhance sales skills.
  • Target Achievement: Meet or exceed business development goals.
Perks/Benefits:
  • This is a commission-based opportunity. Earnings are based on individual production and performance.
  • Potential to earn client member leads
  • Exclusive training/development with the financial services professional supporting you
  • An environment and culture of mutual support and growth
  • Attainment of prestigious credentials and recognition
  • Consistent opportunities for growing your income and character
  • Strong benefits and retirement package
  • Dental, health, and vision insurance
  • Flexible schedule
  • Life insurance
  • Professional development assistance
  • Referral program
Qualifications:
  • Team-Oriented
  • Enthusiastic
  • Positive attitude
  • Self-Starter
  • Community-Focused
  • Coachable
  • Goal-Driven
  • Willingness to obtain state insurance license
  • College degree (preferred, not required)
If you're ready to unleash your competitive drive and embark on a career that changes lives, join our team. 

Flexible work from home options available.