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Insurance Jobs in Chicago, IL (NOW HIRING)

Freeway Insurance

Insurance Sales Manager

Chicago, IL

$17 - $19/hr

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 ...

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Insurance information

See Chicago, IL salary details

$31.9K

$60K

$89.1K

How much do insurance jobs pay per year?

As of Aug 8, 2026, the average yearly pay for insurance in Chicago, IL is $59,952.00, according to ZipRecruiter salary data. Most workers in this role earn between $49,400.00 and $68,500.00 per year, depending on experience, location, and employer.

What are some common challenges faced by professionals working in the insurance industry, and how can they be addressed?

Professionals in the insurance industry often encounter challenges such as staying updated with changing regulations, managing complex client needs, and handling a high volume of claims or policy inquiries. Navigating regulatory changes requires continuous professional development and attention to compliance updates. Effective communication and organizational skills are vital for managing client expectations and workloads efficiently. Building strong relationships with underwriters, claims adjusters, and clients can also help address these challenges and ensure successful outcomes.

What is the difference between Insurance vs Insurance Agent?

AspectInsuranceInsurance Agent
CredentialsVaries by role; may include licenses for specific insurance typesRequires state licensing and certification
Work EnvironmentOffice, online, or client sitesOffice, client meetings, or remote
Employer & IndustryInsurance companies, brokers, agenciesInsurance agencies, brokerages, companies
Job FocusDeveloping, selling, managing insurance policiesSelling insurance policies, client consultation

Insurance is a broad industry encompassing various roles, including Insurance Agents. Insurance Agents specifically focus on selling and advising clients on insurance policies, often requiring licensing. While Insurance professionals may work in different capacities, Insurance Agents are directly involved in client interactions and policy sales, making their roles closely linked but distinct within the industry.

What are the key skills and qualifications needed to thrive in an insurance professional role, and why are they important?

To thrive in an insurance role, you need strong analytical abilities, attention to detail, and a solid understanding of insurance products, often supported by a relevant degree or insurance-specific certifications such as CPCU or CLU. Familiarity with policy management software, customer relationship management (CRM) systems, and underwriting tools is commonly required. Excellent communication, problem-solving skills, and a customer-focused mindset help professionals build trust and effectively address client needs. These competencies are vital for ensuring accurate policy management, regulatory compliance, and delivering high-quality client service in a competitive industry.

What do insurance agents do?

Insurance premium auditors are employees of a variety of companies. You can work with businesses who specialize in handling premium audits, risk management, or business process outsourcing, but most available positions are with insurance companies. You can choose a field based on the type of insurance you’re most familiar with such as workers’ compensation, car, home, or life insurance, or choose a company that works with all insurance types. Some positions require working on the phone, while others require traveling within an assigned geographic area.

What careers are there in insurance?

Careers in insurance include roles such as insurance agents, underwriters, claims adjusters, actuaries, and risk managers. These positions often require strong communication, analytical skills, and industry-specific certifications or licenses. The insurance industry offers opportunities in sales, underwriting, claims processing, and risk assessment across various companies and environments.
More about Insurance jobs
What are the most commonly searched types of Insurance jobs in Chicago, IL? The most popular types of Insurance jobs in Chicago, IL are:
What are popular job titles related to Insurance jobs in Chicago, IL? For Insurance jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Insurance jobs in Chicago, IL look for? The top searched job categories for Insurance jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Insurance jobs? Cities near Chicago, IL with the most Insurance job openings:
Insurance jobs near you
Infographic showing various Insurance job openings in Chicago, IL as of August 2026, with employment types broken down into 91% Full Time, and 9% Part Time. Highlights an 86% In-person, and 14% Remote job distribution, with an average salary of $59,952 per year, or $28.8 per hour.

Insurance Sales Manager

Freeway Insurance

Chicago, IL

$17 - $19/hr

Full-time

Medical, Dental, Vision, Life, Retirement

Posted 10 days ago

Freeway Insurance rating

8.2

Company rating: 8.2 out of 10

Based on 12 frontline employees who took The Breakroom Quiz

141st of 303 rated insurance

Job description

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

Pay Range:

$17 - $19 / 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:

The Store Manager is the driving force behind our business. This exciting position will challenge your sales abilities and give you the opportunity to gain substantial financial rewards, along with mentoring others to achieve the same. We are hiring talented leaders committed to their own success.

  • Lead the sales team’s daily performance and/or targets
  • Expand business by proactively building relationships with existing customers to meet the agreed upon production and active customer goals
  • Coach members of the sales team to deliver a standard of customer care consistently
  • Oversee the sales team to achieve operational targets and monitoring performance
  • Assists with any escalated customer service issues and/or questions that may arise
  • Executes all aspects of Store Operational Excellence (SOE)

The Perfect Match:

  • Personal Lines or Property and Casualty license preferred (but not required)
  • Bilingual in English and Spanish preferred
  • 2 or 4 year college degree or equivalent of experience/education
  • Previous experience leading, coaching, and mentoring sales teams
  • Understanding of fiduciary duty and maintaining high levels of integrity and ethics
  • Ability to build relationships with sales customers
  • Ambitious professional motivated by opportunity for advancement
  • Excellent written and verbal communication skills

Insurance Sales
Insurance Agent
Hiring Immediately
Freeway Auto Insurance

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

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