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Chicago agent

85 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
HUB International
03/03/2026  
AI Product Owner- SPG
About Us Specialty Program Group, a division of HUB International, offers access to capital and investment, deep carrier relationships, creative thinking, product development and broad distribution, while allowing our businesses to maintain the essence of what makes them successful. Specialty Program Group delivers leading-edge specialty expertise backed by transformative digital capabilities and sophisticated data and analytics.   Position Overview We are seeking an AI Product Owner to drive the business use cases, roadmap, and execution of enterprise AI solutions. This critical role sits at the intersection of business, AI technology, development, and user experience; responsible for translating HUB's AI vision into tangible products that deliver measured value. The AI Product Owner will own the product lifecycle for AI; to scale AI adoption from while ensuring responsible AI practices across the enterprise. Key Responsibilities AI Product Strategy & Vision...
HUB International Chicago, IL, USA Full Time
CCC Intelligent Solutions
03/02/2026  
Senior Backend Engineer – DPS Core & Data Engine Squad
Salary range is: $106,277.25 - $140,000.00 This position is bonus and/or commission eligible. CCC Intelligent Solutions Inc. (CCC) is a leading cloud platform for the multi-trillion-dollar insurance economy , creating intelligent experiences for insurers, repairers, automakers, part suppliers, and more. At CCC, we’re making life just work by empowering more than 35,000 businesses with industry-leading technology to get drivers back on the road and to health quickly and seamlessly. We’re pushing boundaries with innovative AI solutions that simplify and enhance the claims and repair journey. Through purposeful innovation and the strength of its connections, CCC technologies empower the people and industry relied upon to keep lives moving forward when it matters most. Learn more about CCC at www.cccis.com .   The Role We are seeking a Senior Backend Engineer who is passionate about database modernization, performance optimization, and strategic refactoring of...
CCC Intelligent Solutions Chicago, IL, USA Full Time
Brown & Brown
03/01/2026  
Senior Benefits Consultant
Built on meritocracy, our unique company culture rewards self-starters and those who are committed to doing what is best for our customers. Brown & Brown is seeking a Senior Benefits Consultant to join our growing team! This role blends thought leadership, market strategy, and high‑impact consulting for the purpose of developing new business. You will shape benefits strategies for major employers while driving new business, expanding relationships, and positioning our firm as a trusted advisor in a competitive marketplace. How You Will Contribute:   Strategic Advisory Serve as the lead strategic advisor for large and mid-sized employers, developing multi‑year health & welfare benefits strategies that improve cost, quality, and employee experience. Guide C‑suite leaders on long‑term healthcare strategies and tactics. Provide insights on emerging market trends, regulatory changes, and innovation within benefits, helping clients stay ahead of...
Brown & Brown Chicago, IL, USA Full Time
Berkley
03/01/2026  
Agency Relationship Specialist
Company Details   Berkley One is a modern insurance provider for a modern generation of affluence. We serve clients who live dynamic, adventurous lives and expect their insurance experience to match. Our mission is to deliver highly personalized risk and claims management through a blend of expert independent agents, cutting-edge digital tools, and the strength of the Berkley brand.   Why Join Us? At Berkley One, you’ll be part of a forward-thinking team that’s reimagining personal insurance. We’re building solutions that are as sophisticated and agile as the clients we serve—individuals and families who value innovation, simplicity, and exceptional service. You’ll collaborate with passionate professionals, leverage modern technology, and help shape the future of our industry.   What We Value A client-first mindset with a passion for delivering exceptional experiences Curiosity, creativity, and a drive to challenge the status...
Berkley Chicago, IL, USA
CNA
02/27/2026  
Underwriting Associate (Underwriting Hub)
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.  JOB DESCRIPTION: Under broad supervision, responsible for underwriting accounts within limited authority. Works independently on a high volume of accounts, applying sound underwriting judgment and collaborating with Underwriters as needed. Partners across the Hub to ensure accurate documentation, pricing execution, and responsive service. This Underwriting Associate position is part of the Underwriting Hub—a growing team designed to provide expanded underwriting capabilities for the organization. We will elevate underwriting excellence through streamlined processes, strategic focus, and collaborative growth that enables our field underwriting teams to deepen agent and broker...
CNA 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
02/13/2026  
Account Manager
About Specialty Program Group: Our goal is to partner with industry-leading specialty businesses to provide them with the ability to achieve their goals and optimize their businesses. Specialty Program Group offers access to capital and investment, deep carrier relationships, creative thinking, product development and broad distribution, while allowing our businesses to maintain the essence of what makes them successful. Specialty Program Group delivers leading-edge specialty expertise backed by transformative digital capabilities and sophisticated data and analytics.  Summary of the Role: A pioneer in insurance technology, Insureon operates the largest online insurance marketplace for small businesses in the U.S. Our proprietary technology platform enables business owners to easily compare and purchase the insurance they need. We also license this platform to select industry participants who are looking to more effectively service their own clients. We are integrated with...
HUB International Chicago, IL, USA Full Time
Arch
02/08/2026  
Executive General Adjuster, Commercial Field Property
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℠. Position Overview Arch Insurance Group Inc., AIGI, has an opening with the Claims Division on the Middle Market Property team as a Executive General Adjuster, Property.  In this role, the responsibilities include handling of first party large property claims including: investigating, evaluating, and negotiating to ensure optimal claim resolution for commercial property claims of high severity and complexity. Provides quality claim handling throughout the claim life cycle (customer contacts, coverage, investigation, evaluation, reserving, negotiation and resolution) including maintaining full compliance with internal and external quality standards and state specific regulations. This...
Arch 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
CNA
01/28/2026  
Senior Software Engineer
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.  We are looking for a highly skilled Senior Python AI Developer with deep expertise in building intelligent agents using Google Vertex AI, particularly with Gemini or OpenAI models. The ideal candidate has a strong foundation in Large Language Models and understands how they work under the hood, combined with experience in evaluating model performance through structured testing methodologies. This role requires proficiency in the technical aspects of agent development while adhering to best practices in prompt engineering, context filtering, and security-aware prompting. The candidate should also have hands-on experience with modern agent frameworks and observability tools, ensuring robust,...
CNA Chicago, IL, USA Full Time
Berkley
01/20/2026  
Associate Underwriter, Casualty
Company Details   What makes Admiral Insurance Group ADMIRABLE .   Since 1974, Admiral Insurance Group has been supporting business innovation and market growth through our wholesale-dedicated excess and surplus (E&S) lines of commercial insurance.  We specialize in underwriting difficult-to-place moderate to high-risk commercial businesses that require creative solutions, outside of the box thinking, entrepreneurial spirit and astute business knowledge.  As a member of the W. R. Berkley Corporation, a Fortune 500® Company and one of the nation’s premier commercial lines property casualty insurance providers, we have the resources, support and industry data to provide exceptional service and exciting solutions for our clients and partners.    Unlock your insure -ability. Learn more about Careers at Admiral Insurance Group .   See what it’s like to work in Admiral's Underwriting Department .   The Company is an equal employment opportunity...
Berkley Chicago, IL, USA

 

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