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Insurance Agent In Training Jobs in Skokie, IL (NOW HIRING)

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Insurance Agent In Training information

See Skokie, IL salary details

$23.9K

$62.1K

$116K

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

As of Aug 9, 2026, the average yearly pay for insurance agent in training in Skokie, IL is $62,087.00, according to ZipRecruiter salary data. Most workers in this role earn between $42,500.00 and $73,500.00 per year, depending on experience, location, and employer.

Why do so many insurance agents quit?

Many insurance agents in training quit due to the challenging nature of building a client base, inconsistent income, and the pressure to meet sales targets. The job often requires strong communication skills, self-motivation, and resilience, which can be difficult for new agents to develop quickly. High turnover is common in the industry, especially during the initial training period.

What are some common challenges faced by insurance agents in training, and how can they be overcome?

Insurance Agents In Training often face challenges such as building a client base from scratch, learning complex insurance products, and meeting sales targets within tight deadlines. Successfully overcoming these challenges typically involves proactive networking, seeking mentorship from experienced agents, and dedicating time to product training and professional development. Many agencies offer structured onboarding programs and regular team meetings to support new agents, helping them develop effective sales strategies and stay motivated as they grow their careers.

What is an insurance agent in training?

Insurance Agents In Training are individuals who are learning the skills and knowledge required to become licensed insurance agents. They typically work under the supervision of experienced agents or managers, assisting with tasks such as client communications, policy research, and sales processes. During this period, they study insurance products, regulations, and sales techniques, and may also prepare for licensing exams. The goal is to gain practical experience and meet all qualifications to become fully licensed insurance agents.

What is the difference between Insurance Agent In Training vs Insurance Agent?

AspectInsurance Agent In TrainingInsurance Agent
Required CredentialsLicensing exam, pre-licensing educationLicensing exam, ongoing continuing education
Work EnvironmentTraining period, supervised salesIndependent or team sales, client meetings
Job ResponsibilitiesLearning policies, shadowing agentsSelling policies, advising clients, managing accounts

The main difference is that an Insurance Agent In Training is in a learning phase, focusing on gaining licensing and experience under supervision, while an Insurance Agent is fully licensed and actively selling insurance policies to clients.

Do insurance agents get paid during training?

Insurance agents in training typically do not receive a salary but may earn commissions or bonuses once they start selling policies. During training, they often focus on studying for licensing exams and gaining product knowledge, with some companies providing stipends or part-time pay. Compensation structures vary by employer and state regulations.

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

To thrive as an Insurance Agent In Training, you need foundational knowledge of insurance products, strong sales acumen, and typically a high school diploma or equivalent, with progress toward state insurance licensure. Familiarity with customer relationship management (CRM) systems, quoting software, and digital communication tools is essential. Outstanding interpersonal skills, resilience, and persuasive communication set top candidates apart in this role. These competencies ensure effective client engagement, regulatory compliance, and the ability to build a successful insurance portfolio.
What cities near Skokie, IL are hiring for Insurance Agent In Training jobs? Cities near Skokie, IL with the most Insurance Agent In Training job openings:
Insurance Agent In Training jobs near you
Infographic showing various Insurance Agent In Training job openings in Skokie, IL as of June 2026, with employment types broken down into 77% Full Time, 18% Part Time, 1% Temporary, and 4% Contract. Highlights an 89% Physical, 1% Hybrid, and 10% Remote job distribution, with an average salary of $62,087 per year, or $29.8 per hour.

Insurance Agent with Training

Boyle Region - Modern Woodmen of America

Oak Park, IL • On-site

$64K - $125K/yr

Full-time

Medical, Dental, Vision, Life, Retirement

Re-posted 15 days ago

Job description

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

Are you someone who has always had a relentless competitive spirit? Do you thrive on challenges and achieving greatness in your career and beyond? The Boyle Region at Modern Woodmen of America is ready to add a new Insurance Agent (future Financial Representative once licensing is achieved) to our team. We are a dedicated group of driven, ambitious professionals, eager to impact people’s lives as we rapidly expand our offices across the region.
The Boyle Region is driven by a clear mission: to select, train, and develop high-caliber individuals who have an developmental spirit and a desire to make a meaningful impact in their communities. We focus on helping representatives build thriving financial services practices through collaboration, authentic relationship-building, and leadership development. Whether it's guiding members toward financial security or mentoring new representatives, our commitment to growth is unwavering. We've qualified for the National Sales Conference 10 years in a row and continue striving toward additional development awards as we expand. Passionate about community impact, we proudly support organizations like Nik’s Wish Foundation, the Baxa Foundation, Enlase, OBSA, Montessori Schools, the American Heart Association, and local food pantries and shelters. Our vision is to grow a purpose-driven team that leads with integrity, serves with heart, and improves lives—both inside and outside the office.
Watch this short video to see how sharing meaningful moments—both personal and professional—can transform perspectives on a career in financial services with Modern Woodmen of America: https://youtu.be/-qWeFzHB-ck
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.
Check out the varying backgrounds of some of our local leaders:
Tim Boyle
Tim is a highly experienced financial services professional with a strong background in cross‑functional team building and strategic sales planning. His leadership experience in developing teams, guiding sales strategy, and supporting professionals at every stage of growth has led him to his role as Regional Director at Modern Woodmen. He is passionate about creating strong, collaborative teams and building meaningful, long‑lasting client relationships.
Bart Warren
Managing Partner, Bart Warren, with Modern Woodmen and has been in this role for 10 years. He began his career in the financial services industry 25 years ago, right out of college, after earning a Marketing and Sales degree from Northern Illinois University in 2000. Bart joined Modern Woodmen in 2009 and quickly moved into leadership. Outside of work, he enjoys coaching his children in travel baseball and softball. He’s been married to his wife for 22 years and is a big fan of the Chicago Cubs and Chicago Bears. In his free time, Bart also enjoys golfing, yardwork, and spending time with his two dogs and cat.
Annie LaMontagna
Annie is an Administrative Assistant at Modern Woodmen, where she's spent almost two years supporting her team through communication, event coordination, and recruiting. She graduated from Illinois State University and enjoyed creating a positive, organized experience for everyone she works with. Outside the office, she loves spending time with my family and friends, reading, and gardening.
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:
  • Strong Income Opportunity. 
  • Potential to earn client member leads. 
  • Once you reach our qualification standards we will consider allocating resources to support you to recruit, train and develop your own team of talented professionals.
  • 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
  • Athletic Background (bonus)
  • Military Background (bonus)
  • 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.