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Chicago life insurance sales agent

26 life insurance sales agent jobs found in Chicago

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
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
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
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
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
Berkley
03/05/2026  
Sr. Production Underwriter - Middle Market
Company Details   Berkley Human Services, a Berkley Company, is devoted to meeting the needs of Human Services Organizations. Our insurance policies are written through our Berkley affiliates, each of which is rated A+ (Superior) by A.M. Best Company with a Financial Category of XV.   We offer property and casualty coverage designed for the unique operational aspects of social service organizations. Our Human Services Program dates back to 1989 and has continuously evolved to meet the unique needs of the market we serve. We insure both nonprofit and for-profit social service organizations, such as child daycare, sheltered workshops, group homes, senior citizen centers, senior independent living, schools, counseling services, YMCAs, YWCAs, and Boys & Girls Clubs. Responsibilities To develop, grow and maintain a profitable book of Human Services business within an assigned territory through marketing and underwriting...
Berkley Chicago, IL, USA
Unum Group
02/28/2026  
Regional Broker Manager, Colonial Life - Chicago/St. Louis
Job Posting End Date: March 13 When you join the team at Unum, you become part of an organization committed to helping you thrive. Here, we work to provide the employee benefits and service solutions that enable employees at our client companies to thrive throughout life’s moments. And this starts with ensuring that every one of our team members enjoys opportunities to succeed both professionally and personally. To enable this, we provide:  Award-winning culture  Inclusion and diversity as a priority  Competitive benefits package that includes: Health, Vision, Dental, Short & Long-Term Disability  Generous PTO (including paid time to volunteer!)  Up to 9.5% 401(k) employer contribution  Mental health support  Career advancement opportunities  Student loan repayment options  Tuition reimbursement Flexible work environments  *All the benefits listed above are subject to the terms of their individual Plans. And that’s just the...
Unum Group Chicago, IL, USA Full Time
Berkley
02/22/2026  
Sr. Production Underwriter - Middle Market (Remote)
Company Details   Berkley Human Services, a Berkley Company, is devoted to meeting the needs of Human Services Organizations. Our insurance policies are written through our Berkley affiliates, each of which is rated A+ (Superior) by A.M. Best Company with a Financial Category of XV.   We offer property and casualty coverage designed for the unique operational aspects of social service organizations. Our Human Services Program dates back to 1989 and has continuously evolved to meet the unique needs of the market we serve. We insure both nonprofit and for-profit social service organizations, such as child daycare, sheltered workshops, group homes, senior citizen centers, senior independent living, schools, counseling services, YMCAs, YWCAs, and Boys & Girls Clubs. Responsibilities To develop, grow and maintain a profitable book of Human Services business within an assigned territory through marketing and underwriting...
Berkley Chicago, IL, USA
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
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
Ryan Specialty
02/10/2026  
Business Development Specialist
Position Summary The Business Development Specialist is responsible for developing new business and retaining current customers by providing them with the best customer service. The role develops and enhances relationships with brokers and agents, coordinates with customers for any ad-hoc requests and addresses their enquiries. They support the business development team and serve as a backup for Business Development Coordinator as needed. What will your job entail? Job Responsibilities: • Analyze current customer accounts, establishing cross-sell/account rounding opportunities. • Develop and maintain relationships with key decision-makers on existing accounts to deepen client engagement and identify potential referrals. • Generate new business leads based on lost accounts, industry listings, networking, and referrals. • Maintain accurate records of sales activities, customer interactions, and pipeline opportunities. • Collaborate with marketing and advertising teams to...
Ryan Specialty Chicago, IL, USA Full Time
Berkley
01/28/2026  
Executive Portfolio Underwriter
Company Details       Berkley Fire & Marine Underwriters was launched in 2013 and is a W. R. Berkley operating unit offering preferred inland marine and related property risks and services. Headquartered in Chicago, Berkley Fire & Marine Underwriters serves customers throughout the United States, both regionally and nationwide.  With the ability to craft customized terms, we provide the most effective protection for those in the construction, logistics, manufacturing and transportation industries.   Our culture is one that empowers employees to question the status quo and seek innovative ways to continue to exceed the expectations of our customers. We practice collaboration, ownership, critical thinking, and a professional growth mindset, along with being part of a larger team daily.   Now more than ever, financial strength is critical to a successful, long term insurance relationship. Berkley Fire & Marine Underwriters is a member...
Berkley Chicago, IL, USA
HUB International
01/18/2026  
Chief Compliance Officer, Risk and Insurance
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   one of the   largest 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...
HUB International Chicago, IL, USA Full Time
Travelers
01/14/2026  
Account Executive/Underwriter, National Accounts
Who Are We? Taking care of our customers, our communities and each other. That’s the Travelers Promise. By honoring this commitment, we have maintained our reputation as one of the best property casualty insurers in the industry for over 170 years. Join us to discover a culture that is rooted in innovation and thrives on collaboration. Imagine loving what you do and where you do it. Job Category Underwriting Compensation Overview The annual base salary range provided for this position is a nationwide market range and represents a broad range of salaries for this role across the country. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment. As part of our comprehensive compensation and benefits program,...
Travelers Chicago, IL, USA Full Time

 

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