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Entry Level Insurance Sales Jobs in Milwaukee, WI

Bankers Life

Wealth Management Trainee

West Allis, WI · On-site

Bankers Life covers your Life & Health coursework to start your insurance sales representative ... This is an entry-level exam administered by the Financial Industry Regulatory Authority (FINRA ...

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All JobsInsurance Sales JobsEntry Level Insurance Sales JobsEntry Level Insurance Sales Jobs in Milwaukee, WI

Entry Level Insurance Sales information

See Milwaukee, WI salary details

$21.7K

$44.3K

$64K

How much do entry level insurance sales jobs pay per year?

As of Sep 6, 2026, the average yearly pay for entry level insurance sales in Milwaukee, WI is $44,343.00, according to ZipRecruiter salary data. Most workers in this role earn between $36,400.00 and $49,200.00 per year, depending on experience, location, and employer.

What is an entry level insurance sales job?

Entry level insurance sales jobs are positions designed for individuals who are new to the insurance industry and have little to no prior experience in sales. These roles typically involve helping clients understand and purchase various types of insurance policies, such as auto, home, life, or health insurance. Employees receive training in sales techniques, product knowledge, and regulatory requirements. The goal is to build strong customer relationships, meet sales targets, and grow a client base while learning the fundamentals of the insurance business.

What skills and qualifications are needed for entry level insurance sales?

To thrive as an Entry Level Insurance Sales representative, you need a high school diploma (or equivalent), basic sales knowledge, and an active state insurance license. Familiarity with CRM software, sales tracking tools, and online quoting systems is often required. Strong interpersonal skills, resilience, and persuasive communication help build client relationships and overcome objections. These skills and qualities are essential for meeting sales targets, ensuring regulatory compliance, and providing excellent customer service.

What are common challenges faced by entry level insurance sales professionals, and how can they be overcome?

Entry-level insurance sales professionals often encounter challenges such as building a client base from scratch, handling rejections, and staying motivated in a commission-driven environment. To overcome these, it's helpful to actively network, seek mentorship from experienced colleagues, and consistently follow up with leads. Developing strong product knowledge and refining communication skills also boost confidence and credibility with potential clients. Many organizations offer training and support to help new agents succeed, so taking advantage of these resources is key.

What is the difference between Entry Level Insurance Sales vs Insurance Agent?

AspectEntry Level Insurance SalesInsurance Agent
Required CredentialsBasic licensing, sales trainingLicensing, certifications, ongoing education
Work EnvironmentOffice, remote, or field salesOffice, client meetings, fieldwork
Employer & Industry UsageInsurance companies, agenciesIndependent agents, agencies, companies
Search & Comparison IntentEntry-level roles, sales trainingExperienced sales, licensing, career growth

Entry Level Insurance Sales typically refers to individuals starting in sales roles with basic licensing and training, often working under supervision. Insurance Agents usually have more experience, licensing, and may operate independently or own agencies. While both roles involve selling insurance products, the key differences lie in experience, independence, and responsibilities.

How to get a job in insurance sales with no experience?

Entry level insurance sales positions often do not require prior experience; instead, employers look for strong communication skills, a customer-focused attitude, and a willingness to learn. Candidates can improve their chances by obtaining relevant certifications, such as a license in insurance sales, and demonstrating enthusiasm during interviews. Training is typically provided on the job, making it accessible for newcomers to enter the field.

Is entry level insurance sales hard?

Entry level insurance sales can be challenging as it requires developing sales skills, understanding insurance products, and building client relationships. Success often depends on communication abilities, persistence, and gaining industry knowledge through training and certifications. The job typically involves a commission-based structure and a learning curve for new representatives.

What are the most commonly searched types of Insurance Sales jobs in Milwaukee, WI?

The most popular types of Insurance Sales jobs in Milwaukee, WI are:

Entry Level Insurance Sales jobs near you
Infographic showing various Entry Level Insurance Sales job openings in Milwaukee, WI as of August 2026, with employment types broken down into 100% Full Time. Highlights an 100% In-person job distribution, with an average salary of $44,343 per year, or $21.3 per hour.

Entry Level Sales Representative - Fast Track Program - Uncapped Commission (Relocation Provided)

Total Quality Logistics

Milwaukee, WI • On-site

$55K/yr

Full-time

Medical, Dental, Vision, Retirement

Re-posted 27 days ago

Key responsibilities

  • Help your account executive solve customer needs, find carriers for time-sensitive freight, and manage daily operations

  • Participate in hands-on and virtual training sessions to develop negotiation skills and build your book of business

  • Use training to meet sales metrics, establish relationships to close new customers, and negotiate prices with customers and carriers

Total Quality Logistics rating

6.0

Company rating: 6.0 out of 10

Based on 116 frontline employees who took The Breakroom Quiz

326th of 366 rated logistics

Job description

General information
Country
USA
State
Wisconsin
City
Milwaukee
Descriptions & requirements
About the role:
The Fast Track Sales Program at TQL is designed for high-potential individuals who want to move faster and earn more than the traditional entry-level path. You'll build a career with an industry leader that offers an award-winning culture, high earning potential with uncapped commission and significant opportunities for advancement.
You'll relocate to Cincinnati to train alongside some of the most successful brokers in the industry, gaining hands-on experience, intensive coaching and real responsibility early in your career. To support your transition, we provide a comprehensive relocation package, Fast Track stipend and a $2,500 sign-on bonus to get you started.
Once you complete training and build a solid book of business, you'll have the opportunity to continue growing in Cincinnati, move into leadership, or relocate to any of TQL's 65+ offices nationwide.
Ready to see how far you can go?
POSITION IS LOCATED IN CINCINNATI - PAID RELOCATION PROVIDED
What's in it for you:
  • $55,000 minimum first-year compensation
    • Includes base salary, sign-on bonus, and Fast Track stipend
  • Uncapped commission opportunity
    • Our average sales representative reaches six-figure earnings within three years
    • Want to know what the top 20% make? Ask your recruiter
  • Relocation package
  • Opportunity to relocate again, nationwide, once you've earned it

What you need:
  • Bachelor's degree required
  • Elite work ethic, 100% in-office
  • Strong negotiation skills with ability to handle conflict
  • Entrepreneurial mindset and exceptional customer service

What you'll be doing:
  • Receive 6 months of direct training from experienced Logistics Account Executives
    • Help your account executive solve customer needs, find carriers for time-sensitive freight and manage daily operations
    • Participate in hands-on and virtual training sessions
    • Develop negotiation skills through prospecting and cold calling
  • Build your book
    • Use your training to meet sales metrics and become eligible for commission
    • Establish relationships to close new customers
    • Negotiate prices with customers and carriers
    • Resolve freight issues to ensure timely pickup and delivery

Why TQL:
  • Certified Great Place to Work with 900+ lifetime workplace awards
  • Clear advancement paths, including leadership opportunities
  • Comprehensive benefits package:
    • Medical, dental, and vision coverage
    • 401(k) with company match
    • Perks including tuition reimbursement, financial wellness planning, employee discounts on gym memberships, pet insurance and more

Why Fast Track:
  • Accelerated development: Reach key milestones faster than a typical entry-level career
  • Additional coaching: More training, support and feedback
  • Top-tier exposure: Learn directly from tenured, high-performing brokers
  • Real ownership: Build your own book of business
  • Career options: Stay in Cincinnati, step into leadership or relocate nationwide

Ideal for recent graduates or those looking to pivot into a high-growth career, this program is demanding by design. It requires commitment, resilience, and a competitive mindset. For those willing to put in the work, Fast Track offers the kind of earning potential, mobility, and career options most people don't reach until much later.
If you thrive in a high-energy environment, set ambitious goals and work relentlessly to achieve them, put your sales career on the Fast Track.
Employment visa sponsorship is unavailable for this position. Applicants requiring employment visa sponsorship now or in the future (e.g., F-1 STEM OPT, H-1B, TN, J1 etc.) will not be considered.
About Us
Total Quality Logistics (TQL) is one of the largest freight brokerage firms in the nation. TQL connects customers with truckload freight that needs to be moved with quality carriers who have the capacity to move it.
As a company that operates 24/7/365, TQL manages work-life balance with sales support teams that assist with accounting, and after hours calls and specific needs. At TQL, the opportunities are endless which means that there is room for career advancement and the ability to write your own paycheck.
What's your worth? Our open and transparent communication from management creates a successful work environment and custom career path for our employees. TQL is an industry-leader in the logistics industry with unlimited potential. Be a part of something big.
Total Quality Logistics is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, age, national origin, genetic information, disability or protected veteran status.
If you are unable to apply online due to a disability, contact recruiting at recruiting@tql.com

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