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Chicago Full Time external wholesaler

17 external wholesaler jobs found in Chicago

AmTrust Financial
11/12/2026  
Executive Underwriter - Primary Casualty
Overview Our Specialty Casualty underwriting department is seeking an Executive Underwriter to join our growing team. The Specialty Casualty team delivers significant value to our wholesale brokers by providing them with an underwriting capability for higher hazard General Liability and Excess insurance needs that are best addressed on an individual risk basis. With this opportunity, you will underwrite and manage a portfolio of hard to place liability risks with tougher exposures considered unique or challenging in accordance with AmTrust E&S guidelines, strategy and profitability standards. The person in this position is responsible for new business development, risk analysis and assessment, coverage evaluation, pricing and contract negotiation in order to maintain and develop a profitable portfolio of non-admitted primary and excess liability risks Professional Liability risks Position requires advanced risk assessment skills with minimum of 15...
AmTrust Financial Chicago, IL Full Time
Ryan Specialty
11/12/2026  
Brokerage Operations Intern
RT Specialty, a division of Ryan Specialty, is a leading wholesale distributor of specialty insurance products and services. Our experienced brokers are specialized in property, casualty, professional lines, transportation and workers’ compensation, providing creative solutions to retail brokerage firms. We define ourselves through our superior execution on behalf of our clients, which has established us as a leader in the industry. Position Summary Ryan Specialty is seeking motivated students to join our Summer 2027 Brokerage Operations Internship, 8-10 weeks, 5 days in office, paid internship designed to provide hands-on exposure to specialty insurance brokerage operations. *The hourly pay rate for this internship is $22/ hour.* Interns will work alongside brokerage professionals, gain insight into client service and operational processes, and develop foundational skills for a career in insurance and risk management. The opportunity is open to candidates based in the...
Ryan Specialty Chicago, IL Full Time
Sompo International
11/12/2026  
Senior Underwriter, Lawyers Professional Liability
Job Description Are you looking for your next opportunity?   Sompo has a unique opportunity for a Senior Underwriter, Lawyers Professional Liability as part of our Sompo Professional Lines team.   Our Sompo Professional Lines Underwriting team offers Lawyers Professional Liability for primary and excess risks. We work through a network of brokers who share our commitment to long-term partnerships built on a strong service proposition.   Location: This position can be based out of our offices in Chicago, IL, New York City, NY, Purchase, NY, Morristown, NJ, Alpharetta, GA, Charlotte, NC, Miami, FL . We strive for collaboration which is why we offer a work environment where our employees thrive and develop long lasting careers. Our business, your impact, our opportunity: What you’ll be doing: Underwriting of Lawyers Professional Liability Experience with admitted or non-admitted LPL products, including working within filed rates, forms and rules,...
Sompo International Chicago, IL Full Time
Ryan Specialty
11/07/2026  
Senior Claims Advocacy Specialist 
RT Specialty, a division of Ryan Specialty, is a leading wholesale distributor of specialty insurance products and services. Our experienced brokers are specialized in property, casualty, professional lines, transportation and workers’ compensation, providing creative solutions to retail brokerage firms. We define ourselves through our superior execution on behalf of our clients, which has established us as a leader in the industry. Position Summary The Senior Claims Advocacy Specialist is responsible for developing and implementing claim analysis and advocacy strategies. The role serves as a subject matter expert on complex issues and collaborates with internal stakeholders to innovate solutions for claims management. They represent the company in high-level negotiations, monitor industry trends, and drive initiatives for operational efficiency and strategic development, fostering strong relationships for organizational success in the specialty insurance market. What...
Ryan Specialty Chicago, IL Full Time
Ryan Specialty
11/05/2026  
Account Executive, Brokerage Operations
RT Specialty, a division of Ryan Specialty, is a leading wholesale distributor of specialty insurance products and services. Our experienced brokers are specialized in property, casualty, professional lines, transportation and workers’ compensation, providing creative solutions to retail brokerage firms. We define ourselves through our superior execution on behalf of our clients, which has established us as a leader in the industry. Position Summary The Account Executive provides account management and operational support to a growing wholesale brokerage team. This role works closely with the Broker to manage new business and renewal activity, prepare accurate market submissions, maintain account documentation, analyze portfolio information, and help ensure the team delivers consistent, responsive service. The ideal candidate is analytical, highly detail-oriented, comfortable working with numbers, and confident using Excel to organize information and identify insights. The...
Ryan Specialty Chicago, IL Full Time
Crum & Forster
11/02/2026  
Senior/Executie Underwriter-Middle Market Solutions Midwest
Crum & Forster Company Overview Crum & Forster (C&F) provides market leading property & casualty, accident & health, specialty and standard commercial lines insurance solutions. A true underwriting company, we have a 200-year history of helping our customers manage risk with laser-focused expertise, integrity and discipline. Our people are empowered to make decisions and   problem-solve with you smartly and swiftly. Our annual gross written premium is 6.2 billion. C&F enjoys a financial strength rating of "A+" (Superior) by AM Best.   Our most valuable asset is our people. We have 3000 employees, and locations throughout the United States and India. With our employee-first focus, the Company is consistently recognized as a great place to work, earning multiple workplace and wellness awards, including the Great Place to Work® Award, Fortune 100 Best Companies to Work For, Fortune Best Workplaces for Parents, Fortune Best...
Crum & Forster Chicago, IL Full Time
Crum & Forster
10/30/2026  
Underwriter, Primary General Liability, Chicago
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 2025 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,...
Crum & Forster Chicago, IL Full Time
Markel
10/26/2026  
Senior Underwriter War & Terrorism
What part will you play? If you’re looking for a place where you can make a meaningful difference, you’ve found it. The work we do at Markel gives people the confidence to move forward and seize opportunities, and you’ll find your fit amongst our global community of optimists and problem-solvers. We’re always pushing each other to go further because we believe that when we realize our potential, we can help others reach theirs. Join us and play your part in something special! The primary purpose of this position is to underwrite new business and renewals in a profitable manner and according to authority level and established guidelines, and participate in special projects having an impact on the business. Assigned larger and more important agents/brokers. Utilize underwriting tools to determine accurate classifications, rates, and premium charges. Understand state laws, including cancellation and non-renewal, within assigned territory to properly transact business within each...
Markel Chicago, IL Full Time
Sompo International
10/24/2026  
Sr. Underwriter, Cyber/E&O Underwriting, Sompo Pro
As a leading provider of insurance and reinsurance with worldwide operations and employees in Bermuda, U.S., U.K., Continental Europe and Asia, we recognize that our success is derived directly from those who matter the most: our people . At Sompo International, our values of integrity, collaboration, agility, execution and excellence underpin our culture and our commitment to providing an employee experience that attracts and engages the best talent in the industry. As we continue to grow, we strive to find diverse, innovative and driven professionals to join our teams and offer a broad range of career and development opportunities at all levels, in multiple business areas, in each of our locations throughout the world.  Our compensation and benefits programs are market driven and competitive, with excellent family friendly policies and flexible working provisions. Job Description Are you looking for your next opportunity? Sompo has a unique opportunity for a Senior...
Sompo International Chicago, IL Full Time
Ryan Specialty
10/23/2026  
Business Solutions Director
RT Specialty, a division of Ryan Specialty, is a leading wholesale distributor of specialty insurance products and services. Our experienced brokers are specialized in property, casualty, professional lines, transportation and workers’ compensation, providing creative solutions to retail brokerage firms. We define ourselves through our superior execution on behalf of our clients, which has established us as a leader in the industry. Position Summary The Business Solutions Director is a key function for RT Specialty, maintaining the overall goals and vision of their workstream as it pertains to technology and operational strategy. The Business Solutions Director will set the roadmap for the year while also demonstrating ability to quickly change as outside factors arise. The Business Solutions Director will consistently drive ideas forward while creatively push the boundaries on solutions, keeping in mind increased efficiency, ease of use, and flexibility as key factors for...
Ryan Specialty Chicago, IL Full Time
Ryan Specialty
10/20/2026  
Senior Operations, Controls & Carrier Compliance Specialist
RT Specialty, a division of Ryan Specialty, is a leading wholesale distributor of specialty insurance products and services. Our experienced brokers are specialized in property, casualty, professional lines, transportation and workers’ compensation, providing creative solutions to retail brokerage firms. We define ourselves through our superior execution on behalf of our clients, which has established us as a leader in the industry. Position Summary The Senior Operations, Controls, and Carrier Compliance Specialist will support special projects throughout RT operations, primarily associated with carrier contract adherence. This position will also support day to day support of our carrier compliance and control framework. This position works closely with IT teams, RT Brokerage and Binding management, and other Business Shared Service teams. The position will need to be familiar with contracts (carrier contracts experience preferred), IT systems and will need to have strong...
Ryan Specialty Chicago, IL Full Time
RLI
10/14/2026  
Sr. Underwriter - Executive Products (Wholesale)
About Us  We’re not like other insurance companies. From our specialty products to our business model, our culture to our results — we’re different. Different is who we are, and how we work, interact, deliver and succeed together. Creating a different and better insurance experience doesn’t just happen. It takes focus and a shared passion for going beyond the expected to forge relationships and deliver care that makes a difference. This approach rises from and is supported by our talented, ethical and smart team of employee owners united around a single purpose: to work alongside our customers and partners when they need us, in unexpected ways, with exceptional results. Apply today to make a difference with us.  RLI is a Glassdoor Best Places to Work company with a strong, successful background. For decades, our financial track record has been stellar — a testament to our culture and validation of our reputation as an excellent underwriting company....
RLI Chicago, IL Full Time
Arch
10/14/2026  
Underwriting Manager
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 Summary: The Medical Malpractice Underwriting Manager on the Central Miscellaneous Facility team will be responsible for new and renewal business, help the team maintain and grow the book of business, and manage direct reports. This will be a hybrid position in Chicago, IL. Responsibilities and Accountabilities: Underwrite and maintain Healthcare Medical Malpractice new business and renewal accounts. Develop underwriting solutions, determine insurability, calculate appropriate premium, and thoroughly document files. Prepare quotations and binds business with a particular emphasis on assessing risk and reaching premium goals as determined by the division head. Sustain...
Arch Chicago, IL Full Time
AmTrust Financial
10/09/2026  
Vice President, Underwriting
Overview The VP, Underwriting role is an experienced professional that should have a proven track record of leading functional leaders and teams and building profitable commercial lines books distributed via independent agencies, brokers, and wholesale partners, targeting small, middle-market and complex risks across various targeted industries. classes. The VP, Underwriting will be a “hands-on” technical expert focused on targeting a wide variety of commercial risks throughout the U.S. across. This individual maintains a solid understanding of AmTrust’s mission, vision, and values. Upholds the standards of the AmTrust organization. Reports to the Vice President – Midwest Region and has Underwriting responsibility across the 12 Midwest States: IL, IN, IA, KY, MI, MN, MO, ND, OH, SD, WI and WV Responsibilities · Leads leaders and a team that underwrites a profitable book of small, middle market and complex risks, employing the...
AmTrust Financial Chicago, IL Full Time
Ryan Specialty
10/09/2026  
Broker Assistant, ProExec
RT Specialty, a division of Ryan Specialty, is a leading wholesale distributor of specialty insurance products and services. Our experienced brokers are specialized in property, casualty, professional lines, transportation and workers’ compensation, providing creative solutions to retail brokerage firms. We define ourselves through our superior execution on behalf of our clients, which has established us as a leader in the industry. Position Summary The Broker Assistant provides operational and administrative support to a dynamic Professional & Executive Liability (ProExec) brokerage team, helping ensure the accurate and timely processing of insurance transactions throughout the policy lifecycle. This role assists with policy administration, endorsements, quoting, binder issuance, account documentation, and servicing activities while partnering closely with brokers, carrier partners, and internal teams. This is an excellent opportunity for a recent college graduate or...
Ryan Specialty Chicago, IL Full Time
Ryan Specialty
08/29/2026  
Senior Business Analyst
RT Specialty, a division of Ryan Specialty, is a leading wholesale distributor of specialty insurance products and services. Our experienced brokers are specialized in property, casualty, professional lines, transportation and workers’ compensation, providing creative solutions to retail brokerage firms. We define ourselves through our superior execution on behalf of our clients, which has established us as a leader in the industry. Position Summary The Senior Business Analyst will support strategic business initiatives including RT Specialty’s technical solution and business processes. This position will be a vital link between our solutions and our business objectives and will be responsible for the identification, management, and implementation of business processes and digital solutions leading to increased efficiency and integration in all areas of RT Specialty. You will be tasked to lead or participate in multiple, complex projects utilizing and leveraging your own...
Ryan Specialty Chicago, IL Full Time
CNA
08/16/2026  
Underwriting Consultant, Wholesale Allied Healthcare Facilities
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.  Individual contributor responsible for the overall management, business development, analysis and monitoring of a highly complex book of business. Recognized as a technical expert in an underwriting specialty. Under general management direction, works within broad limits of authority on assignments requiring a high degree of technical complexity and coordination. May have regional, industry segment or company-wide scope. JOB DESCRIPTION: Essential Duties & Responsibilities Performs a combination of duties in accordance with departmental guidelines: Works on highly complex underwriting risks employing diagnostic and systematic analysis to assess acceptability. Develops...
CNA Chicago, IL Full Time

 

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