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Chicago Full Time insurance sales agent

32 insurance sales agent jobs found in Chicago

Freeway Insurance Services America
02/17/2026  
Insurance Sales Agent - Customer Service
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...
Freeway Insurance Services America Chicago, IL, USA Full Time
Freeway Insurance Services America
02/17/2026  
Insurance Sales Agent - Customer Service
Sign-On Bonus Opportunity of up to $1,000* 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,...
Freeway Insurance Services America Chicago, IL, USA Full Time
Freeway Insurance Services America
02/17/2026  
Insurance Sales Agent - Customer Service
Sign-On Bonus Opportunity of up to $1,000* 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,...
Freeway Insurance Services America Chicago, IL, USA Full Time
Freeway Insurance Services America
02/17/2026  
Insurance Sales Agent - Customer Service
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...
Freeway Insurance Services America Chicago, IL, USA Full Time
Freeway Insurance Services America
02/17/2026  
Insurance Sales Agent - Customer Service
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...
Freeway Insurance Services America Chicago, IL, USA Full Time
Freeway Insurance Services America
02/17/2026  
Insurance Sales Agent - Customer Service
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...
Freeway Insurance Services America Chicago, IL, USA Full Time
Freeway Insurance Services America
02/17/2026  
Insurance Sales Agent - Customer Service
Sign-On Bonus Opportunity of up to $1,000*  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,...
Freeway Insurance Services America Chicago, IL, USA Full Time
Freeway Insurance Services America
02/17/2026  
Insurance Sales Agent - Customer Service
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...
Freeway Insurance Services America Chicago, IL, USA Full Time
Freeway Insurance Services America
02/17/2026  
Insurance Sales Agent - Customer Service
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...
Freeway Insurance Services America Chicago, IL, USA Full Time
CRC Group
02/21/2026  
Broker Assistant
The position is described below. If you want to apply, click the Apply button at the top or bottom of this page. You'll be required to create an account or sign in to an existing one. If you have a disability and need assistance with the application, you can request a reasonable accommodation. Send an email to Accessibility (accommodation requests only; other inquiries won't receive a response). Regular or Temporary: Regular Language Fluency:  English (Required) Work Shift: 1st Shift (United States of America) Please review the following job description: Serves as a partner to Broker providing superior support regarding all policies and key accounts. Provides high quality service to agents and companies. ESSENTIAL DUTIES AND RESPONSIBILITIES Following is a summary of the essential functions for this job. Other duties may be performed, both major and minor, which are not mentioned below. Specific activities may change from time to time. 1....
CRC Group Chicago, IL, USA Full Time
Freeway Insurance Services America
02/17/2026  
Insurance Sales Manager
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...
Freeway Insurance Services America Chicago, IL, USA Full Time
HUB International
02/01/2026  
AI Product Owner
Job Description ABOUT US  At HUB International, we are a team of entrepreneurs. We believe in protecting and supporting the aspirations of individuals, families, and businesses. We help our clients evaluate their risks and develop solutions tailored to their needs. We believe in empowering our employees to learn, grow, and make a difference. Our structure enables our teams to maintain their own unique, regional culture while leveraging support and resources from our corporate centers of excellence. HUB is a global insurance and employee benefits broker, providing a boundaryless array of business insurance, employee benefits, risk services, personal insurance, retirement, and private wealth management products and services. With over $5 billion in revenue and almost 20,000 employees in 600 offices throughout North America, HUB has grown substantially, in part due to our industry leading success in mergers and acquisitions.  Position Overview HUB is...
HUB International Chicago, IL, USA Full Time
The Hartford
11/14/2025  
Excess Casualty Wholesale Account Manager
Account Manager - OA09HN We’re determined to make a difference and are proud to be an insurance company that goes well beyond coverages and policies. Working here means having every opportunity to achieve your goals – and to help others accomplish theirs, too. Join our team as we help shape the future.              This role will have a Hybrid work schedule, with the expectation of working in an office (Chicago, IL, Scottsdale, AZ, Frisco, TX, Greenwood Village, CO, Morristown, NJ, New York, NY) 3 days a week (Tuesday through Thursday). The Account Manager, as part of Global Specialty Operations, will serve as a critical partner to the Primary Casualty and Excess Casualty Wholesale underwriting teams. The individual focuses on service experience & book of business management, while also acting as a key contact for brokers and underwriters. This is an individual contributor role without supervisory responsibilities, also mentors and train less experienced...
The Hartford Chicago, IL, USA Full Time
Crum & Forster
10/23/2025  
VP, Middle Market Solutions Underwriting MidWest
Crum & Forster Company Overview Crum & Forster (C&F) , with a proud history dating to 1822, provides specialty and standard commercial lines insurance products through our admitted and surplus lines insurance companies. C&F enjoys a financial strength rating of "A+"(Superior) by AM Best and is proud of our superior customer service platform. Our claims and risk engineering services are recognized as among the best in the industry. Our most valuable asset is our people: more than 2000 employees in locations throughout the United States. The company is increasingly winning recognition as a great place to work, earning several workplace and wellness awards, including the 2024 Great Place to Work® Award  for our employee-first focus and our steadfast commitment to diversity, equity and Inclusion. C&F is part of Fairfax Financial Holdings, a global, billion dollar organization.  For more information about Crum & Forster, please visit...
Crum & Forster Chicago, IL, USA Full Time
CNA
08/24/2025  
AVP, Underwriting (Technology Industry Segment P&C)
You have a clear vision of where your career can go. And we have the leadership to help you get there.  At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential.  For over three decades, CNA has been a trusted provider of insurance solutions for technology companies of all sizes—from emerging startups to global enterprises—across software, IT services, hardware, media, and telecommunications. Our Global Technology Practice delivers specialized coverage including Technology Errors & Omissions (Tech E&O), Cyber Liability, comprehensive international solutions, to complement our traditional Property & Casualty lines. With deep industry expertise, flexible capabilities, and a collaborative approach, we design innovative insurance programs tailored to the unique needs of each client. CNA remains the carrier of choice for our valued agent and...
CNA Chicago, IL, USA Full Time
H.W. Kaufman Group
02/27/2026  
Commercial Lines Underwriter
Responsibilities Build, maintain, and grow a book of business Manage agency relationships and serve as lead client contact Create and execute marketing plan to increase new and renewal business Rate, quote and bind each risk to determine acceptability, coverage, and pricing for large or complex renewals as well as new business Develop and submit underwriting referrals to company brokerage facilities and Burns & Wilcox management   Monitor key metrics to formulate corrective action impacting new business hit, renewal retention, premium growth, and loss ratio Lead, train, and develop Assistant and Associate Underwriters Qualifications Bachelor’s degree or equivalent combination of education and experience   Minimum 3 years of commercial lines underwriting or brokerage experience required, excess & surplus experience preferred Demonstrated proficiency in sales and marketing...
H.W. Kaufman Group Chicago, IL, USA Full Time
Arch
02/19/2026  
AVP, Business Development
With a company culture rooted in collaboration, expertise and innovation, we aim to promote progress and inspire our clients, employees, investors and communities to achieve their greatest potential. Our work is the catalyst that helps others achieve their goals. In short, We Enable Possibility℠. This position is directly accountable for the following responsibilities:  Drive regional business development priorities with Arch’s business units and agency/broker partners that support growth strategies. Utilize internal and external data platforms to analyze progress of priorities; when appropriate, recommend refinement of priorities to more appropriately align with current market environment. Serve as a point of contact for agents/brokers in the region for product support, appetite awareness, quality service, opportunity assessments, and the overall fulfilment of multiline needs. Support generation of new and manage current relationships to meet or exceed revenue goals...
Arch Chicago, IL, USA Full Time
H.W. Kaufman Group
02/13/2026  
Underwriter, Private Client
  *This position is open to multiple Burns & Wilcox branch offices across the US.*   When retail agents and brokers have successful clients who require coverage for the unique, the unusual, or the unconventional, they come to the Private Client Practice at Burns & Wilcox. Our Underwriters have full underwriting authority to build and grow a profitable book of Private Client business across the US and Canada.  Burns & Wilcox offers unparalleled resources and exposure for those looking to excel in the specialty insurance career.  Interested? Join our team! Responsibilities Build a growing book of profitable Private Client business Manage agency relationships and serve as lead client contact Provide a Best in Class customer service experience for our retail partners Execute on the national marketing strategy to increase new and renewal business Work within granted authority and program guidelines to...
H.W. Kaufman Group Chicago, IL, USA Full Time
Liberty Mutual
02/12/2026  
Wholesale Distribution Director - West Region
Description Advance your Career at Liberty Mutual Insurance - A Fortune 100 Company!   Liberty Mutual Group is a diversified global financial services company headquartered in Boston, MA. Our company, which is one of the largest Property and Casualty insurers in the US., employs over 50,000 people in more than 900 offices around the world.    At Liberty Mutual, we work with both retail and wholesale agents and brokers, and our wholesale-dedicated Ironshore brand engages in the US wholesale market. Ironshore is looking to hire a Wholesale Branch Executive whose territory will cover the Central and Western US (inclusive of Chicago and Texas) in addition to managing select national wholesale broker relationships. You will work with key brokers to drive profitable growth and represent the Ironshore and Global Risk Solutions (GRS) brand and all business segments that engage in the wholesale market. Additionally, they will partner with internal...
Liberty Mutual Chicago, IL, USA Full Time
Ryan Specialty
02/11/2026  
Director, Products & Underwriting
Position Summary RT Connector, a division of Ryan Specialty, is seeking a Director of Products & Underwriting within our Wholesale division to join our Chicago, IL office. We are a fast-paced, energetic, and rapidly growing organization offering an excellent opportunity for individuals looking to advance their careers. This role is pivotal in positioning RT Connector as the premier solution for digitalized insurance capacity in the U.S. wholesale market. The Director of Products & Underwriting will play a multifaceted role, with a strong emphasis on building and cultivating insurance capacity on the Connector platform. Key responsibilities include product delivery, client and carrier stewardship, strategic planning, and the execution of various platform solutions. The Product Manager will lead the strategy, development, and execution of RT Connector’s admitted standard lines marketplace, delivering innovative solutions tailored to the needs of retail agents. This...
Ryan Specialty Chicago, IL, USA Full Time

 

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