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Entry Level Inbound Insurance Sales Jobs in Chicago, IL

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Entry Level Inbound Insurance Sales information

See Chicago, IL salary details

$9

$21

$37

How much do entry level inbound insurance sales jobs pay per hour?

As of Jun 24, 2026, the average hourly pay for entry level inbound insurance sales in Chicago, IL is $21.04, according to ZipRecruiter salary data. Most workers in this role earn between $15.87 and $24.76 per hour, depending on experience, location, and employer.

What are some common challenges faced by entry-level inbound insurance sales representatives, and how can they be overcome?

Entry-level inbound insurance sales representatives often encounter challenges such as handling a high volume of customer inquiries, adapting quickly to new products and policies, and overcoming initial rejections from potential clients. Success in this role requires patience, active listening, and the ability to build rapport over the phone. Many companies provide comprehensive training programs and mentorship to help new hires develop product knowledge and effective sales techniques. Consistent practice, seeking feedback from experienced team members, and staying up-to-date with industry trends can greatly improve confidence and performance in this position.

What are the key skills and qualifications needed to thrive as an Entry Level Inbound Insurance Sales representative, and why are they important?

To thrive as an Entry Level Inbound Insurance Sales representative, you need strong communication, active listening, and persuasive sales abilities, typically supported by a high school diploma or equivalent. Familiarity with CRM software, call center systems, and obtaining relevant state insurance licenses are often required. Standout candidates excel in building rapport, handling objections calmly, and demonstrating resilience under pressure. These skills are vital for effectively converting leads, meeting sales targets, and providing excellent customer service in a competitive insurance environment.

What are entry level inbound insurance sales jobs?

Entry level inbound insurance sales jobs involve assisting customers who contact an insurance company, typically by phone or online, to inquire about or purchase insurance products. Representatives in these roles answer questions, explain policy details, and help customers choose the best insurance options for their needs. Since the position is 'inbound,' you respond to incoming requests rather than making cold calls. This job is ideal for those new to insurance sales, as it often includes training and provides an opportunity to learn about different insurance products and sales techniques.
What are the most commonly searched types of Inbound Insurance Sales jobs in Chicago, IL? The most popular types of Inbound Insurance Sales jobs in Chicago, IL are:
Entry Level Inbound Insurance Sales jobs near you

Insurance Sales Agent - Customer Service

Freeway Insurance

Chicago, IL • On-site

$16 - $18/hr

Full-time

Medical, Dental, Vision, Life, Retirement

Posted 18 days ago

Freeway Insurance rating

8.0

Company rating: 8.0 out of 10

Based on 10 frontline employees who took The Breakroom Quiz

145th of 261 rated insurance

Job description

Sign-On Bonus Opportunity of up to $1,000*

Pay Range:

$16 - $18 / hour

Our Perks:

  • Unlimited/Uncapped commission
  • Lucrative incentive sales plans, bonuses and sales contests
  • No Cold Calling- We have a high volume of inbound sales leads and walk in traffic
  • Comprehensive paid training and licensing with continuous on-going training and mentorship
  • Recognition culture
  • Comprehensive Benefits package including medical, dental, vision and life insurance
  • Retirement Plan: A 401K plan with a percentage of company-matched contributions
  • Fitness: We reimburse up to $15 a month to an employee for their gym
  • Employee Assistance Program: Confidential assistance to you or anyone in your household who is experiencing personal or professional problems — at no cost
  • Extra Perks: Access to disability, hospital indemnity, health advocate program, universal life, critical illness, and accident insurance plans. We even offer pet insurance

Our Company:

Confie and its family of companies - Freeway, Baja, Bluefire & others - is one of the largest privately held insurance brokers in the United States and has been ranked the #1 Personal Lines Leader by the Insurance Journal for the seventh straight year!. With over 800 retail store locations to choose from nationwide, we encourage you to take your career and income potential to new heights! We are proactively looking for bright, talented, and motivated individuals who are goal oriented and excited for career advancement. Come Grow With Us!

What You Will Do:

As an Insurance Agent you will be responsible primarily for the sale of nonstandard auto insurance to new and existing customers.

  • Solicit new business and maintain current business levels in order to achieve or exceed sales production goals.
  • Expand business by proactively building relationships with existing customers to meet the agreed upon production goals.
  • Accurate accounting of all currency transactions as well as timely delivery of deposits to the bank with scanned documentation in agency management system.
  • Connects very quickly; builds and leverages client relationships. Ability to educate and advise the customer on which products best fit their needs

The Perfect Match:

  • Personal Lines or Property and Casualty license preferred (but not required)
  • Bilingual in English and Spanish preferred
  • Sales or customer service experience
  • High School Diploma or GED
  • Ability to build relationships with sales customers
  • Excellent follow-up and multi-tasking skills
  • Ambitious professional motivated by opportunity for advancement
  • Excellent written and verbal communication skills

Insurance Sales
Insurance Agent
Hiring Immediately
Freeway Auto Insurance

CBU

As permitted by applicable law and from time-to-time, Confie may use a computer system that has elements of artificial intelligence to help make decisions about your employment, including recruitment, hiring, renewal of employment, or the terms and conditions of your employment. Employees with questions about Confie’s use of these computer systems should contact Human Resources at employeerelations@confie.com

What Freeway Insurance employees say

Pay

Hours and flexibility

Workplace

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