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Chicago senior underwriter employee benefits

58 senior underwriter employee benefits jobs found in Chicago

Ascot Group
04/16/2026  
Senior Underwriter, Commercial Surety
This is an opportunity to join Ascot Group - one of the world’s preeminent specialty risk underwriting organizations. Designed as a modern-era company operating through an ecosystem of interconnected global operating platforms, we’re bound by a common mission and purpose: One Ascot. Our greatest strength is a talented team who flourish in a collaborative, inclusive, and entrepreneurial culture, steeped in underwriting excellence, integrity, and a passion to find a better way, The Ascot Way. The Ascot Way guides our people and our organization. Our underwriting platforms collaborate to find creative ways to deploy our capital in a true cross-product and cross-platform approach. These platforms work as one, deploying our capital creatively through our unique Fusion Model: Client Centric, Risk Centric, Technology Centric. Built to be resilient, Ascot maximizes client financial security while delivering bespoke products and world-class service — both pre-and post-claims....
Ascot Group Chicago, IL Full Time
Ascot Group
04/16/2026  
Senior Underwriter, Commercial Surety
This is an opportunity to join Ascot Group - one of the world’s preeminent specialty risk underwriting organizations. Designed as a modern-era company operating through an ecosystem of interconnected global operating platforms, we’re bound by a common mission and purpose: One Ascot. Our greatest strength is a talented team who flourish in a collaborative, inclusive, and entrepreneurial culture, steeped in underwriting excellence, integrity, and a passion to find a better way, The Ascot Way. The Ascot Way guides our people and our organization. Our underwriting platforms collaborate to find creative ways to deploy our capital in a true cross-product and cross-platform approach. These platforms work as one, deploying our capital creatively through our unique Fusion Model: Client Centric, Risk Centric, Technology Centric. Built to be resilient, Ascot maximizes client financial security while delivering bespoke products and world-class service — both pre-and post-claims....
Ascot Group Chicago, IL Full Time
Liberty Mutual
04/15/2026  
Executive Underwriter, Cyber Technology Errors & Omissions
Description Ironshore’s Cyber Retail team is seeking an experienced underwriter to support a growing retail portfolio focused on Primary Cyber, Tech E&O, and related cyber liability products. This role underwrites SME, middle‑market, and select large‑complex risks placed through retail brokers in the Midwest.  The ideal candidate has strong retail broker relationships, takes initiative to source and develop new submissions, and can independently underwrite accounts across a range of sizes and complexities while maintaining consistent underwriting discipline and portfolio-focused decision-making.   Responsibilities   Manages portfolio of brokers/agents & clients. Leverages market presence and expertise to develop and underwrite profitable business, acting as a representative for Liberty. Has relationships with senior/market-leading brokers and/or key agents. Maintains a strong market presence, including established relationships with agents...
Liberty Mutual Chicago, IL Full Time
Liberty Mutual
04/08/2026  
Executive Underwriter, Wholesale Miscellaneous Professional Liability
Description Executive Underwriter — Miscellaneous Professional Liability: Acts as the leading technical authority for Miscellaneous Professional Liability (MPL) across an aligned wholesale territory, working independently and autonomously subject to required process oversight. Serves as the go‑to advisor on MPL coverage, exposures and wordings for colleagues across the segment, including senior underwriting leaders. Underwrites MPL policies within delegated authority, making acceptance and declination decisions based on analytical, data‑driven assessment of submitted information and pricing the risk appropriately. Typical exposures include E&O claims for consultants, IT/service providers and other non‑class specific professionals, media/communications risks, and other miscellaneous advisory or service professions. Where applicable, may be responsible for setting the business plan and portfolio strategy for the MPL book in their territory. Responsibilities...
Liberty Mutual Chicago, IL Full Time
Tokio Marine HCC
04/08/2026  
Senior Underwriter, Cyber
About TMHCC Tokio Marine HCC (TMHCC) brings 50 years of service to the specialty insurance industry, today offering over 100 products to commercial customers in 180 countries around the world. Every policy we write is special, enabling our clients to do amazing things. From insuring the crops that feed us to the rock concerts that entertain us, to rescuing international travelers in trouble. Organic growth and over 60 successful acquisitions have grown our 2023 Gross Written Premium (GWP) to over $7.5 Billion. Our workforce has grown to 4,300 worldwide … big, but not so big that you cannot make a difference. Our Good Company values, including integrity, empowerment, and commitment to customer service, and a culture of innovation, communication, and collaboration make TMHCC a great place to work. What We Offer ·         Competitive salary and employee benefit package ·         Strong learning culture ·         Growth perspectives ·         6% 401K match ·         20 days...
Tokio Marine HCC Chicago, IL Full Time
QBE
03/26/2026  
Senior Underwriter - Private NFP D&O
Primary Details Time Type: Full time Worker Type: Employee The Opportunity: The purpose of this role is to support the implementation of specific business strategies by contributing to business development and growth through cultivating relationships with designated clients and making informed underwriting decisions to enhance the profitability of the portfolio. Key responsibilities involve generating new business, retaining renewals, and ensuring the overall profitability of our Private NFP D&O business within our Specialty insurance vertical. •        Location: Chicago, IL - Denver, CO •        Work Arrangement: hybrid or remote working expectations •         The starting salary for this role is between $109,000.00 and $164,000.00 Your new role Review, evaluate and price business by applying underwriting judgment and adhering to regulations. Identify and minimize risks through due diligence and escalation of issues when...
QBE Chicago, IL Full Time
BP&C, Shared Services Inc. (American National & Argo Group)
03/25/2026  
VP, Underwriting, Workers' Compensation
Company Argo Group Argo Group is an underwriter of specialty insurance products in the property and casualty market. Argo offers a full line of products and services designed to meet the unique coverage and claims-handling needs of businesses. The Argo entities are wholly-owned subsidiaries of Clearbrook Group Holdings Inc. Job Description Summary: To provide strategic guidance and direction to the underwriting business units in regard to business development, underwriting excellence, and operational/shared services to promote profitable underwriting results. Responsible for driving profitable growth for assigned product or territory. Collaborates with executive management to develop strategic and tactical initiatives to reach the organization’s goals. The primary duties and responsibilities of the role are: · Identify and support profitable new business and product opportunities. · Identify strategic agencies and facilitate effective partnerships with...
BP&C, Shared Services Inc. (American National & Argo Group) Chicago, IL Full Time
Liberty Mutual
03/19/2026  
Senior Underwriter, Middle Market Multi-Industry
Description We are seeking an experienced Middle Market Senior Underwriter to underwrite commercial property & casualty risks in the middle market segment. As an individual contributor, you will make analytical, data-driven underwriting decisions within delegated authority, with limited guidance from leadership. You will evaluate and price moderately complex to complex accounts (including high individual line sizes and unusual exposures in parts of North America), manage broker and client relationships, and help shape product and portfolio strategy for your line of business. To be considered for this role, candidates must reside within the specified geographic location. This position requires regular in-person visits with local brokers and agents, so remote hires outside the designated territory cannot be accommodated. Key Responsibilities Underwrite middle market commercial accounts within assigned authority by assessing submissions, reviewing...
Liberty Mutual Chicago, IL Full Time
AIG
03/15/2026  
Senior Executive Underwriter - National Accounts, Excess Casualty
Join us as a Senior Executive Underwriter - National Accounts, Excess Casualty to step up to a key team leadership role that will drive business growth. Make your mark in Underwriting AIG underwriting teams help to find insurance solutions in areas including Financial Lines, Property, Casualty, Specialty Lines, Cyber, Multinational Clients, and High Net Worth individuals. We are reimagining how we help customers to manage risk, transforming our operating model, and reshaping our role responsibilities and career pathways. The goal is to unlock the full potential in each colleague – empowering our people to grow as insurance professionals and add more value to our customers and AIG. How you will create an impact AIG is seeking a Senior Underwriting Specialist, National Accounts Excess Casualty to contribute to their industry leading Excess Casualty underwriting team.  AIG’s strong foundation as the market leader in this area has evolved through its long-term...
AIG Chicago, IL Full Time
Huntington
12/19/2025  
Commercial P&C Insurance Sales Executive Senior - Chicago, IL
Description Summary: The Insurance Sales Executive Senior – Commercial P&C is a high-impact, commission-based sales role offering significant income potential. This position requires strong consultative selling skills, effective communication, and a deep understanding of the insurance industry. We provide a comprehensive three-year income transition plan to support your success from day one. The ideal candidate will be skilled in pursuing and closing sales in the Commercial Property and Casualty space, particularly with clients in the $50M–$500M+ revenue range. Expertise across all lines of commercial P&C insurance—including loss sensitive and group captive insurance programs—is essential. A strong focus on business development and strategic growth is critical to success in this role. Key Responsibilities: Drive business development by identifying and cultivating new client opportunities through internal...
Huntington Chicago, IL Full Time
AIG
11/23/2025  
Executive Underwriter, AIGRM
At AIG, we are reimagining the way we help customers to manage risk. Join us as an Executive Underwriter, AIG Risk Management (AIGRM) to play your part in that transformation. It’s an opportunity to grow your skills and experience as a valued member of the team. Make you mark in Underwriting AIG underwriting teams help to find insurance solutions in areas including Financial Lines, Property, Casualty, Specialty Lines, Cyber, Multinational Clients, and High Net Worth individuals. We are reimagining how we help customers to manage risk, transforming our operating model, and reshaping our role responsibilities and career pathways. The goal is to unlock the full potential in each colleague – empowering our people to grow as insurance professionals and add more value to our customers and AIG. How you will create an impact The Executive Underwriter will be responsible for underwriting the Workers’ Compensation, General Liability and Auto Liability primary Casualty...
AIG Chicago, IL Full Time
AIG
09/11/2025  
Actuary & AVP - Retail and Canada Property Pricing
Actuary & AVP - Retail and Canada Property Pricing At AIG, we are reimagining the way we help customers to manage risk. Join us as a Actuary & Assistant Vice President - Retail and Canada Property Pricing to take on key responsibilities within a world-class actuarial function. Make your mark in Actuarial Our Actuaries are on the front lines, quantifying risk, pricing insurance and reserving losses for AIG’s major insurance operating companies, globally. We collaborate with Finance, Claims, Operations, Marketing and Risk Management, among other functions. As an AIG actuary, you will be challenged and encouraged to reach your greatest potential to help improve how we predict, manage and mitigate risk. How you will create an impact We are seeking an actuarial professional with industry expertise to lead the Retail Property pricing team.  The individual will partner with the business and support teams on strategy, risk selection, pricing, and portfolio...
AIG Chicago, IL Full Time
Sompo International
08/17/2025  
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
AIG
07/14/2025  
Underwriting Specialist, Casualty
Underwriting Specialist, Casualty Make your mark in Underwriting AIG underwriting teams help to find insurance solutions in areas including Financial Lines, Property, Casualty, Specialty Lines, Cyber, Multinational Clients, and High Net Worth individuals. We are reimagining how we help customers to manage risk, transforming our operating model, and reshaping our role responsibilities and career pathways. The goal is to unlock the full potential in each colleague – empowering our people to grow as insurance professionals and add more value to our customers and AIG. How you will create an impact This level underwriter typically handles accounts/clients that are most complex.   Has a greater underwriting authority and handles larger accounts and/or more complex risks than the Senior Underwriter. The role will be responsible for underwriting NA Casualty - (i.e. WC, AL, USL&H) Develops and manages underwriting strategies for both renewals and prospects within...
AIG Chicago, IL Full Time
AIG
06/25/2025  
Senior Executive Underwriter, AIGRM
At AIG, we are reimagining the way we help customers to manage risk. Join us as a Senior Executive Underwriter to play your part in that transformation. It’s an opportunity to grow your skills and experience as a valued member of the team. Make your mark in AIG Risk Management, AIGRM. AIG underwriting teams help to find insurance solutions in areas including Financial Lines, Property, Casualty, Specialty Lines, Cyber, Multinational Clients, and High Net Worth individuals. We are reimagining how we help customers to manage risk, transforming our operating model, and reshaping our role responsibilities and career pathways. The goal is to unlock the full potential in each colleague – empowering our people to grow as insurance professionals and add more value to our customers and AIG. How you will create an impact This role may supervise a group of Senior and Associate Underwriters, including designing and monitoring work, development of underwriting and/or marketing...
AIG Chicago, IL Full Time
AIG
04/16/2025  
Senior Regional Production Specialist, Lexington Healthcare
At AIG, we are reimagining the way we help customers to manage risk. Join us as a Senior Regional Production Specialist, Lexington Healthcare to play your part in that transformation. It’s an opportunity to grow your skills and experience as a valued member of the team. Lexington Insurance 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 Produce, underwrite, manage and service a profitable book of miscellaneous medical facilities and allied healthcare business. Utilize...
AIG Chicago, IL Full Time
Crum & Forster
03/28/2025  
Senior Underwriter - Middle Market Solutions
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" (Excellent) 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 visit...
Crum & Forster Chicago, IL Full Time
HUB International
04/22/2026  
Account Manager - Complex Risk
About HUB In a rapidly changing world, HUB advises businesses and individuals on how to prepare for the unexpected. As one of the world’s largest insurance brokers, our focus is dedicated to providing our customers with the peace of mind that what matters most will be protected — through unrelenting advocacy and tailored insurance solutions that put our clients in control. Our growing team of professionals across North America represents a broad, deep, and one-of-a kind aggregation of entrepreneurs and leaders recognized for their excellence throughout the insurance community. Why Choose HUB? Throughout our network of more than 550 HUB offices in North America, we offer a competitive, exciting, and friendly work environment that strategically positions our employees for longevity and success. At HUB, we believe in investing in the future of our employees and provide continuous opportunities for growth and development .   Our entrepreneurial culture fosters an environment...
HUB International Chicago, IL Full Time
BP&C, Shared Services Inc. (American National & Argo Group)
04/22/2026  
Sr. Reinsurance Accountant
Company Shared Services Argo Group is an underwriter of specialty insurance products in the property and casualty market. Argo offers a full line of products and services designed to meet the unique coverage and claims-handling needs of businesses. The Argo entities are wholly-owned subsidiaries of Clearbrook Group Holdings Inc. Job Description Business Title(s): Sr. Reinsurance Analyst  Employment Type: Full-Time  FLSA Status: Exempt  Location: In-Office  Summary:    The Senior Reinsurance Analyst is responsible for the accurate and timely accounting, analysis, and reporting of reinsurance activity in compliance with GAAP, statutory requirements, and Sarbanes-Oxley controls, supporting the monthly, quarterly, and year-end close processes. The role serves as the primary point of contact for intermediaries, reinsurers, auditors, and internal stakeholders, managing reinsurance reporting, claim communications, coverage inquiries, and collections while...
BP&C, Shared Services Inc. (American National & Argo Group) Chicago, IL Full Time
Huntington
04/20/2026  
Director - Leveraged Finance Execution (HCA)
Description The Director - Leveraged Finance Execution, in conjunction with Huntington’s Capital Markets, Investment Banking and Sponsor Coverage, evaluates credit opportunities, mitigates associated risks, structures, and underwrites financial sponsor and leveraged finance transactions for Huntington’s private equity and corporate clients across multiple specialty industry and client coverage groups, delivering the Bank’s balance sheet capital commitments in support of these transactions. Additionally, as part of the Huntington Capital Advisors (HCA) sub-team, this role will focus on executing transactions for privately held businesses, including founder-owned, family office–owned, and small-cap sponsor-backed companies. Typical client needs include strategic capital solutions such as shareholder lifecycle planning, inorganic growth initiatives, value creation strategies, monetization events, capital raises, and...
Huntington Chicago, IL Full Time

 

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