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Chicago employee benefits sales

92 employee benefits sales jobs found in Chicago

The Standard
06/25/2026  
EB National Accounts Training Consultant
The next part of your journey is right around the corner — with The Standard. A genuine desire to make a difference in the lives of others is the foundation for everything we do. With a customer-first mindset and an intentional focus on building strong teams, we’ve been able to uphold our legacy of financial stability while investing in new, innovative technologies that support the needs of our customers. Our high-performance culture focused on operational excellence thrives thanks to remarkable people united by compassion and a customer-first commitment. Are you ready to make a difference? This is an exciting new opportunity to make a big impact! We are looking for an experienced Employee Benefits National Accounts Sales and/or Account Management, to make a slight career shift and become our new Training & Development Specialist in our National Accounts and large case space! You must have performed in a National Accounts role w/ ancillary EB products to be...
The Standard Chicago, IL Full Time
Liberty Mutual
06/25/2026  
Senior Underwriter, Major Accounts Property – Shared and Layered
Description Our Senior Underwriter contributes to the growth and profitability of assigned Shared & Layered Retail Property accounts through marketing, underwriting and managing of products and services of complex risks. Risks may require special handling or unusual coverages. Requires specialized knowledge of underwriting concepts, practices, procedures and techniques to include coverage issues, product lines, marketing, relevant systems, and competition in the marketplace. Demonstrates strong strategic and marketing capabilities.   This is a hybrid office role in the posted office location.   Responsibilities:   Establishes and maintains relationships to facilitate marketing of Liberty Mutual Shared & Layered Retail Property products and services to the brokerage community. Makes independent sales calls to market and cross market. Reviews and negotiates policy terms and conditions including manuscript wording. Underwrites...
Liberty Mutual Chicago, IL Full Time
Liberty Mutual
06/25/2026  
Senior Underwriter, Wholesale Management Liability
Description   Our Financial Lines Underwriting Team is seeking a highly motivated individual with strong analytical and sales skills to fill a Senior Underwriter opportunity on our Commercial D&O team in Chicago to focus on growing our wholesale brokerage book of business.    This position is a wholesale focused Senior underwriter role that will contribute to the growth and profitability of our Private, Not-For-Profit, and Public Directors & Officers, Employment Practices, and Fiduciary Liability product lines through marketing, underwriting, and general product management.  Some risks may require special handling or unusual coverages, including manuscript policy development. The position demonstrates functional technical knowledge of relevant underwriting concepts, practices, procedures, and techniques, to include; coverage issues, multiple product lines, marketing, relevant systems, and competition in the market place. Strong Midwest wholesale...
Liberty Mutual Chicago, IL Full Time
Freeway Insurance Services America
06/24/2026  
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 Full Time
QBE
06/23/2026  
Senior Specialist Financial Lines Claims
Primary Details Time Type: Full time Worker Type: Employee Senior Specialist Financial Lines Claims Location: USA – Multi Office Locations (Chicago, Atlanta, New York, and Plano Work Arrangement: Hybrid   The salary range for this role is:  $99,000-$186,00K The Opportunity Manages the complete investigation, evaluation and resolution of assigned portfolio of complex claims emanating from Professional Lines business segments, including lawyers and miscellaneous professionals. Engages, directs and manages external advisors and vendors including legal service professionals, discovery vendors, data and security experts and consultants across highly complex portfolio of matters. Your New Role • Manage a diverse portfolio of complex claims which includes conducting fact, liability and loss investigations and interpreting insurance contracts in an effective and efficient manner •Evaluate and negotiate the resolution of assigned claims in a...
QBE Chicago, IL Full Time
Crum & Forster
06/22/2026  
Senior Underwriter - Commercial Surety 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...
Crum & Forster Chicago, IL Full Time
Unum Group
06/22/2026  
Client Manager Associate
Job Posting End Date: June 28 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 Full Time
Origami Risk
06/22/2026  
Sales Development Representative
Overview As a Sales Development Representative (SDR) you will be responsible for seeking new business opportunities by fielding all inbound marketing leads. You will use your communication skills to cultivate strong relationships with potential clients. Our strongest SDR's are highly motivated, results driven, and possess a competititve work drive. This is a hybrid role based out of our Chicago office.   Starting base pay for this role is $55,000. The actual base pay is dependent upon many factors, such as transferable skills, work experience, business needs, training, location, and market demands. The base pay range is subject to change and may be modified in the future. This role will be eligible for a bonus as well as competitive medical, dental, and vision benefits, wellness reimbursement, life insurance, and a 401(k) with company match. We offer vacation and sick leave benefits (under a flexible time off policy in most states)....
Origami Risk Chicago, IL Full Time
AIG
06/18/2026  
Regional Production Specialist Sr, Excess & Surplus Lines
Join us as a Senior Regional Production Specialist to grow your career at the forefront of Lexington Healthcare insurance. Make your mark in Lexington Healthcare AIG’s Lexington Insurance Company is the leading US-based surplus lines insurer. For over 50 years, it has provided flexible solutions to companies and organizations of all sizes – from Fortune 100 corporations to small and middle market entities. Lexington is renowned for its ability to help brokers find solutions to the most challenging insurance needs of their clients. Drawing on their entrepreneurial spirit, colleagues are encouraged each day to rise to challenges and embrace opportunities to make a difference. How you will create an impact The Senior Regional Production Specialist manages all Healthcare underwriting within an assigned Branch Office and handles referral decisions for the most complex portfolios. This role takes on a strategic component in the development, implementation and evaluation of...
AIG Chicago, IL Full Time
Liberty Mutual
06/16/2026  
Wholesale Management Liability Senior Underwriter
Description     Our Financial Lines Underwriting Team is seeking a highly motivated individual with strong analytical and sales skills to fill an Senior/Executive Underwriter opportunity on our Commercial D&O team in Chicago to focus on growing our wholesale brokerage book of business.      This position is a wholesale focused executive underwriter role that will contribute to the growth and profitability of our Private, Not-For-Profit, and Public Directors & Officers, Employment Practices, and Fiduciary Liability product lines through marketing, underwriting, and general product management.  Some risks may require special handling or unusual coverages, including manuscript policy development. The position demonstrates functional technical knowledge of relevant underwriting concepts, practices, procedures, and techniques, to include; coverage issues, multiple product lines, marketing, relevant systems, and competition in the market place. Strong...
Liberty Mutual Chicago, IL Full Time
Applied Systems
06/16/2026  
Manager, Solution Consulting - Cytora
Job Description Make a Difference at Ivans     Digital connectivity is the lifeblood of innovation. At Ivans, a division of Applied, we are at the heart of what is driving innovation across the entire insurance ecosystem. Making a difference – for the industry and within our team – is what pushes us to do better each day. That’s why we’re building a team that shows up every day ready to learn, willing to try new things, and driven to deliver innovative software and services that make us indispensable to our customers – all within a culture built on values that make us indispensable to each other too.    Position Overview      We’re searching for a Manager, Solution Consulting – Cytora  to lead and develop our carrier-focused Solution Consulting team. In this role, you will manage a team of Solution Consultants who partner with our Ivans, Cytora and Applied sales teams to serve carrier, MGA and adjacent market customers in a consultative,...
Applied Systems Chicago, IL
Freeway Insurance Services America
06/15/2026  
Insurance Sales Agent - Customer Service
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: Discount gym membership to over 12,200 fitness centers and 9,300 on-demand workout videos including a $15 a month reimbursement. 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...
Freeway Insurance Services America Chicago, IL Full Time
Freeway Insurance Services America
06/15/2026  
Insurance Sales Agent - Customer Service
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: Discount gym membership to over 12,200 fitness centers and 9,300 on-demand workout videos including a $15 a month reimbursement. 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...
Freeway Insurance Services America Chicago, IL Full Time
Independence Pet Group
06/14/2026  
Principal Engineer, Agentic Journey Engineering Lead
Established in 2021,   Independence Pet Holdings   is a corporate holding company that manages a diverse and broad portfolio of modern pet health brands and services, including insurance, pet education, lost recovery services, and more throughout North America.   We believe pet insurance is more than a financial product and build solutions to simplify the pet parenting journey and help improve the well-being of pets. As a leading authority in the pet category, we operate with a full stack of resources, capital, and services to support pet parents. Our multi-brand and omni-channel approach include our own insurance carrier, insurance brands and partner brands.  Role Summary   We are seeking a forward-thinking Enterprise Principal Engineer to drive the development and deployment of autonomous AI agents on the Microsoft Copilot Studio (M365) platform, with a strong emphasis on Power Apps, Power Automate, Dynamics 365, and Azure AI services.  This role is...
Independence Pet Group Chicago, IL Full Time
Pet Partners Pet Insurance
06/14/2026  
Principal Engineer, Agentic Journey Engineering Lead
Established in 2021,   Independence Pet Holdings   is a corporate holding company that manages a diverse and broad portfolio of modern pet health brands and services, including insurance, pet education, lost recovery services, and more throughout North America.   We believe pet insurance is more than a financial product and build solutions to simplify the pet parenting journey and help improve the well-being of pets. As a leading authority in the pet category, we operate with a full stack of resources, capital, and services to support pet parents. Our multi-brand and omni-channel approach include our own insurance carrier, insurance brands and partner brands.  Role Summary   We are seeking a forward-thinking Enterprise Principal Engineer to drive the development and deployment of autonomous AI agents on the Microsoft Copilot Studio (M365) platform, with a strong emphasis on Power Apps, Power Automate, Dynamics 365, and Azure AI services.  This role is...
Pet Partners Pet Insurance Chicago, IL Full Time
Freeway Insurance Services America
06/11/2026  
Insurance Sales Agent - Customer Service
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: Discount gym membership to over 12,200 fitness centers and 9,300 on-demand workout videos including a $15 a month reimbursement. 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...
Freeway Insurance Services America Chicago, IL Full Time
Freeway Insurance Services America
06/11/2026  
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 Full Time
Freeway Insurance Services America
06/11/2026  
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 Full Time
Freeway Insurance Services America
06/11/2026  
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 $10 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 Full Time
Freeway Insurance Services America
06/11/2026  
Insurance Sales Agent - Customer Service
Sign-On Bonus Opportunity of up to $1,000* Pay Range: $15 - $17 / 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 Full Time

 

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