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Chicago sales and service insurance agent

26 sales and service insurance agent jobs found in Chicago

Freeway Insurance Services America
08/28/2026  
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
08/26/2026  
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
08/26/2026  
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
HUB International
08/03/2026  
Marketing Specialist
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 every major U.S. carrier, manage over $400M in premium annually and are licensed in all 50 states. We place a high value on having fun at work, personal and company integrity and teamwork, and we believe our success is truly a team sport. We foster a service mentality inside and outside our company and our fast-paced team is driven by results and is energetic about servicing our clients. We believe that our team members know what work location will enable them to do their best work in serving our customers. As an eCommerce workplace, we have prioritized working as...
HUB International Chicago, IL Full Time
Freeway Insurance Services America
08/28/2026  
District Sales Manager
Starting pay at $65,000 base plus monthly bonus and annual bonus opportunities,  Our Perks: Commission & Bonus Eligibility Recognition Culture & Leadership Development Competitive Vacation & Sick Time Package 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, Baja, Bluefire & others - is one of the largest privately held insurance brokers in the United States and has been...
Freeway Insurance Services America Chicago, IL Full Time
Berkley
08/24/2026  
AVP, Head of Cyber- Cyber Risk Engineer
Company Details   Berkley Cyber Risk Solutions provides first and third-party cyber coverage for emerging cyber exposures, complemented by pre and post breach services. A team of experienced professionals delivers comprehensive cyber coverage and data breach protection to commercial insureds of all sizes and industries. Our singular focus of viewing cyber as a peril allows us to constantly refine and update new coverage options for emerging risks and trends and be responsive to client specific coverage and service needs.   BerkleyShield is an innovative insurtech embedded withing Berkley Cyber Risk Solutions, focused on transforming the SME cyber insurance market through technology, data, and proactive risk management. Our platform helps organizations better understand, mitigate, and insure cyber risk while enabling brokers and partners to deliver faster, smarter cyber coverage solutions. Responsibilities A successful...
Berkley Chicago, IL
Unum Group
08/22/2026  
Sales Consultant Associate- Chicago (Summer 2027 Start Date)
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 beginning…   With...
Unum Group Chicago, IL Full Time
Ryan Specialty
08/22/2026  
VP of Sales - Employee Benefits
Position Summary The VP of Sales – Employee Benefits, is responsible for commanding territory performance and exceeding targets, through a culture of efficiency and innovation. The role collaborates across the enterprise to grow the benefits business. They shape industry discussions, ensure unwavering compliance with regulations, mitigate potential challenges and maximize profitability. What will your job entail? Position Summary: The VP of Sales – Employee Benefits, is responsible for commanding territory performance and exceeding targets, through a culture of efficiency and innovation. The role collaborates across the enterprise to grow the benefits business. They shape industry discussions, ensure unwavering compliance with regulations, mitigate potential challenges and maximize profitability. Location: Remote or Hybrid (based on location) Position Responsibilities: Develops and executes strategic vision and direction for the offices across...
Ryan Specialty Chicago, IL Full Time
Core Specialty
08/09/2026  
Commercial Surety Regional Manager
- The Commercial Surety Regional Manager is responsible for the underwriting, marketing, production, profitability, and overall management of a regional Commercial Surety portfolio. This position serves as the senior underwriting leader for the assigned territory and is accountable for achieving premium growth, underwriting profitability, agency development, and portfolio management objectives. The Regional Manager will develop and maintain strong relationships with agents, brokers, principals, indemnitors, and other business partners while exercising significant underwriting authority and ensuring compliance with company underwriting guidelines and risk appetite. The position is highly market-facing and focused on profitable business development, agency management, and underwriting execution. Key Accountabilities/Deliverables: Underwriting Leadership Serve as lead underwriter for the assigned territory. Analyze, evaluate, and approve commercial surety...
Core Specialty Chicago, IL Full Time
Travelers
07/30/2026  
Executive Underwriter / Senior Account Executive Officer - Northfield (E&S) Brokerage Casualty
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 Full Time
Travelers
07/29/2026  
Account Executive Officer/Sr. 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 Full Time
Liberty Mutual
07/27/2026  
Premium Auditor I
Description Our professional auditors are integral to our company's mission by ensuring the financial integrity of premium development. In this role, you will examine policyholders' operations and financial records to ensure exposures (such as payroll, sales, fixed assets) are accurately calculated within strict insurance guidelines and communicate audit findings through detailed formal reports. As a Premium Auditor, you will work out of your home, when not traveling to policyholders' locations.   Responsibilities: Perform examination of policyholders' accounting and financial records to ensure accurate calculation of earned premium for smaller, less complex risks. Ensure that audited exposures (payroll, sales, fixed assets, etc.) are accurately calculated within strict insurance guidelines. Communicate audit findings through detailed formal reports supported by audit workpapers. Qualifications Review...
Liberty Mutual Chicago, IL Full Time
CNA
07/24/2026  
Underwriting Consultant, National Accounts Casualty Wholesale
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: Join this elite team of Excess Casualty Underwriters who are high level individual contributors handling wholesale lead umbrella and excess accounts. Recognized as a technical expert, you will drive business results through strong sales, marketing and relationship building skills with external and internal business partners. You are responsible for overall management, business development, growth and profitability of a book business. This position works from our office in a hybrid capacity from our office in Chicago, IL. Essential Duties & Responsibilities Reviews applications and financial requirements for risks requiring complex underwriting skills....
CNA Chicago, IL Full Time
Travelers
07/18/2026  
Account Executive Officer, Senior Underwriter - Loss Sensitive, Large Projects
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 Full Time
CNA
07/16/2026  
VP, Regional Underwriting Manager Midwest (Core Middle Market)
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.  CNA is looking for a strategic and experienced underwriting leader to lead and grow our Core Middle Market business in the Midwest region. As the Regional Underwriting Manager, you will develop underwriting talent, drive underwriting excellence, strengthening portfolio performance across multiple products, and deliver sustainable, profitable growth across the region. This highly visible leadership role offers the opportunity to shape business strategy, build trusted partnerships, and make a meaningful impact within an organization that values leadership, accountability, and long-term success. JOB DESCRIPTION: Essential Duties & Responsibilities Performs a combination of duties...
CNA Chicago, IL Full Time
Hiscox
07/09/2026  
Senior Underwriter, Professional Risks
Job Type: Permanent Build a brilliant future with Hiscox   Drive growth with an ambitious team of MPL Underwriters at Hiscox Position: Sr. Underwriter Reporting to Regional Manager – MPL The Role: Hiscox USA is currently searching for a dynamic, engaging and solutions-oriented Sr. Underwriter to drive new professional liability business and complex renewal business within the MPL sector in the West Coast region. This position provides a unique opportunity for a professional liability specialist to join a fast paced, dynamic team to write policies tailored to the specific requirements of the MPL sector. Lines of business include commercial general liability, professional liability (E&O) and cross-sold Cyber from time to time. We also specialize in accountants, real estate agents, property managers, trustees, consultants, freight forwarders, staffing firms, TPAs, associations, and more! Risks vary greatly in size and complexity (from start-ups to...
Hiscox Chicago, IL Full Time
Travelers
07/09/2026  
Global/Multinational Commercial Underwriter, Account Executive
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 Full Time
CCC Intelligent Solutions
07/08/2026  
Pricing Strategy Manager
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 The Pricing Strategy Manager is responsible for defining and executing pricing and monetization strategies for a portfolio of AI-powered solutions. This...
CCC Intelligent Solutions Chicago, IL Full Time
H.W. Kaufman Group
07/04/2026  
Senior Underwriter, Commercial Insurance
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 Full Time
Berkley
06/30/2026  
Sr. Production Underwriting (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 coverages 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   Company URL: https://www.berkleyhumanservices.com/                     For highly qualified candidates who are not located within a 50-mile radius of the Minneapolis or Chicago...
Berkley Chicago, IL

 

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