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40 middle market jobs found

Crum & Forster
03/16/2026  
VP, Middle Market Solutions Underwriting 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 visit...
Crum & Forster Chicago, IL, USA Full Time
Sompo International
03/15/2026  
Senior Underwriter, Middle Market
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...
Sompo International Chicago, IL, USA Full Time
MarshMcLennan
03/08/2026  
Senior Account Manager - Middle Market Employee Health & Benefits: Self-Funding Expert
Company: Marsh McLennan Agency Description: About Marsh McLennan Agency Midwest  Marsh McLennan Agency’s Midwest Region is a full-service brokerage providing business insurance, employee benefits, private client insurance, and retirement services to businesses and individuals across the country. MMA Midwest is consistently recognized as a top workplace, attracting and retaining its insurance talent by rewarding expertise and investing in career development. Colleagues enjoy an award-winning culture that fosters a highly productive and results-driven working environment. A day in the life. As a Senior Account Manager, your role is to ensure the successful delivery of services to clients by creating and implementing customized service plans. You are responsible for building strong relationships with clients, understanding their needs, negotiating coverage, and managing proposals and renewals.  You will also engage in strategic planning for clients, understanding the...
MarshMcLennan Schaumburg, 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
Flagstar Bank
02/28/2026  
Group Manager - Middle Market (Chicago, IL)
Position Title Group Manager - Middle Market (Chicago, IL) Location Work From Home IL, IL 62629 Job Summary Responsible for the building and leadership of a team who focuses on new business development, portfolio management, credit quality, and overall relationship management of their portfolio of clients targeting the Chicago, IL area. Ensures the generation of revenue by cultivating commercial relationships with companies of revenues between $30MM to $1Bln. This leader will be the point person in the market. Pay Range: $165,621 - $223,588 - $281,556 Pay Range: Local Minimum Wage - $0.00 - $0.00 Job Responsibilities: Strategic Planning :  Partnering with regional leadership to create a strategic plan for the Commercial Group and creating action plans to ensure the achievement of the plan including setting and tracking individualized goals for each team member in regards to production and revenue, and forecasting results for management based on existing...
Flagstar Bank IL, USA Full Time
Liberty Mutual
02/24/2026  
Executive Underwriter, Middle Market Multi-Industry
Description The Senior Underwriter for Middle Market Multi-Industry underwrites policies within underwriting authority, with limited guidance from leadership as needed. Makes decisions on whether to underwrite business by making analytical, data-driven decisions based on data and information provided, including pricing the risk.   Responsibilities   Manages portfolio of brokers/agents and clients. Leverages market presence and knowledge to develop and underwrite profitable business, acting as a representative for Liberty. Maintains a strong market presence, including established relationships with agents and brokers. Looks to strengthen these relationships and develop new ones. Contributes ideas for product development and participates in development and execution. Contributes to team projects (e.g., process / tool improvement). Understands the work implications of relevant legislation and regulation. Collaborates effectively across teams, stakeholders,...
Liberty Mutual Chicago, IL, USA Full Time
CNA
01/31/2026  
Underwriting Consultant(Middle Market Private Equity)
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, USA Full Time
Sompo International
01/07/2026  
AVP - Underwriter Team Lead, Middle Market
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...
Sompo International Chicago, IL, USA Full Time
Ryan Specialty
05/17/2025  
Assistant Vice President, Middle Market Business (MMB) Underwriting
Position Summary We are seeking a dynamic and experienced Assistant Vice President (AVP) of Middle Market Business (MMB) to lead a high-performing property underwriting team and manage a significant book of Property Commercial Lines business. This is a dual-role opportunity where you will serve as both a top-tier Underwriter and a strategic people leader. If you want to be part of a forward-thinking organization that values innovation and leadership and to make a tangible impact on business performance, we encourage you to apply today! What will your job entail? Key Responsibilities Underwriting Leadership : Manage a $40-60M book of new and renewal business, ensuring risk acceptability, pricing accuracy, and adherence to underwriting guidelines. Agency Relationships : Cultivate and maintain strong relationships with agency partners across assigned territories. Team Development : Lead, coach, and mentor a team of Underwriters and Underwriting Assistants,...
Ryan Specialty Chicago, IL, USA 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, USA Full Time
Sompo International
03/17/2026  
Underwriter, Sompo Pro – Small Business & Middle Markets
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 an...
Sompo International Chicago, IL, USA Full Time
Risk Strategies
03/16/2026  
Regional Brokerage Leader
The Regional Brokerage Leader (RBL) serves as a strategic partner between regional teams and national resources, ensuring consistent placement strategy execution, effective carrier relationships, and efficient use of wholesaler channels. The RPL leads with a "Fewer and Stronger" carrier engagement philosophy and plays a critical role in overseeing placement decisions, driving carrier growth, and managing carrier and wholesaler performance within their designated region. Key Responsibilities: 1. Strategic Understanding, Communication & Execution Promote and execute the "Fewer and Stronger" placement strategy across the region in a proactive and retroactive manner to ensure execution. Serve as the conduit between National Placement Leadership and regional teams, ensuring alignment and consistency. 2. Carrier Growth & Performance Monitor and support a 10% growth target with core carrier partners across the region. Partner with National Placement to identify and...
Risk Strategies IL, USA Full Time
Brown & Brown
03/13/2026  
Associate Underwriter
Built on meritocracy, our unique company culture rewards self-starters and those who are committed to doing what is best for our customers. Nexus Specialty Inc. is seeking an Associate Underwriter to join our growing team in Chicago, IL ! The underwriter will play a key role working with the product leader to help grow a profitable book of business for companies in the larger middle market and corporates segment.  The underwriter will take an active part in the development and implementation of an underwriting strategy that identifies profitable market opportunities and broker relationships. How You Will Contribute:   Underwrite, manage and develop a book of primary and excess renewal business Partner with the product leader to review and manage overall book performance and production results. Analyze risks and book of business results to manage and control underwriting exposure and pricing strategy consistent with MGA/carrier objectives. Manage retail...
Brown & Brown Chicago, IL, USA Full Time
Hiscox
03/06/2026  
VP, Product & Underwriting Practice Leader - Management Liability
Job Type: Permanent Build a brilliant future with Hiscox   VP, Product & Underwriting Practice Leader - Management Liability Reports to: SVP, Corix and Head of Strategic Integration Location: NYC, Atlanta, Chicago, Hartford, Los Angeles, Boston Band: III Travel: Up to 25%   Team: Works closely with cross-functional stakeholders including SPADE, marketing, distribution development, claims, actuarial, underwriting operations, as well as the CUO org. Role Overview: The VP, Product & Underwriting Practice Leader is a strategically critical leader responsible for driving profitable growth and technical excellence across our Corix business. This role combines product management and underwriting leadership, overseeing the full product lifecycle, risk selection, and innovation for both digital and intermediated channels. The successful candidate will own and deliver the P&L for their product(s) by setting vision and strategy, driving strong...
Hiscox Chicago, IL, USA Full Time
Hiscox
03/06/2026  
AVP/VP, Product & Underwriting Practice Leader - Property & Casualty
Job Type: Permanent Build a brilliant future with Hiscox   AVP/VP, Product & Underwriting Practice Leader-Property & Casualty Reports to: SVP, Corix and Head of Strategic Integration Location: NYC, Atlanta, Chicago, Hartford, Los Angeles, Boston Band: III Travel: Up to 25%   Team: Works closely with cross-functional stakeholders including SPADE, marketing, distribution development, claims, actuarial, underwriting operations, as well as the CUO org. Role Overview: The AVP/VP, Product & Underwriting Practice Leader is a strategically critical leader responsible for driving profitable growth and technical excellence across our Corix business. This role combines product management and underwriting leadership, overseeing the full product lifecycle, risk selection, and innovation for both digital and intermediated channels. The successful candidate will own and deliver the P&L for their product(s) by setting vision and strategy,...
Hiscox Chicago, IL, USA Full Time
Hiscox
03/06/2026  
AVP/VP, Product & Underwriting Practice Leader - Technology & Cyber
Job Type: Permanent Build a brilliant future with Hiscox   AVP/VP, Product & Underwriting Practice Leader-Technology & Cyber Reports to: SVP, Corix and Head of Strategic Integration Location: NYC, Atlanta, Chicago, Hartford, Los Angeles, Boston Band: III Travel: Up to 25%   Team: Works closely with cross-functional stakeholders including SPADE, marketing, distribution development, claims, actuarial, underwriting operations, as well as the CUO org. Role Overview: The AVP/VP, Product & Underwriting Practice Leader is a strategically critical leader responsible for driving profitable growth and technical excellence across our Corix business. This role combines product management and underwriting leadership, overseeing the full product lifecycle, risk selection, and innovation for both digital and intermediated channels. The successful candidate will own and deliver the P&L for their product(s) by setting vision and strategy,...
Hiscox Chicago, IL, USA Full Time
Reliance Matrix
03/04/2026  
Director - Field Operations
Job Responsibilities and Requirements Position open to any Regional Sales Office. The Director, Field Operations leads the service support team within National and Middle Market, developing and monitoring performance metrics, fostering employee development, and ensuring seamless service for complex clients. Collaborates with National and Middle Market teams to achieve growth, persistency, and profitability goals. Operational: Assess areas of improvement such as training needs, team assignments, process enhancements, workflows, and performance management risks. Partner with National Accounts leaders to continuously evaluate staffing and training needs and opportunities to improve overall operating efficiency.  Lead and participate in strategic initiatives and projects Manage Field operations Supervisor Provide training and on boarding support as needed Assist in the development of and adherence to Field Operations Standard Operating Procedures. Will ensure best...
Reliance Matrix Schaumburg, IL, USA Full Time
CNA
02/21/2026  
Underwriting Specialist, Multinational P&C Central to West Coast
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: The CNA International platform brings together all the assets of CNA – global network, broad product array, underwriting expertise, superior service and technology – and weaves these strengths into innovative solutions to meet middle market customer needs around the world. That’s why a growing number of businesses with international exposures are turning to CNA to help them manage their increasingly complex global property, casualty and professional risks. This hybrid role will work from our office in Chicago, IL. Essential Duties and Responsibilities: Underwriting Expertise ·   Reviews applications and financial requirements to determine acceptability of...
CNA Chicago, IL, USA Full Time
Arch
02/14/2026  
Director, Multi Line Risk Engineer
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℠. Job Summary The Director, Multi Line Risk Engineer is responsible for conducting Middle Market field surveys and providing service support. This role involves both on-site physical surveys and virtual/phone surveys, with a focus on detailed assessment of operations, exposures, and control adequacy. The position aims to protect the future of the company and ensure profitability through timely delivery of industry-leading safety and risk management solutions. Responsibilities Conduct on-site and virtual/phone surveys of prospects and clients evaluating complex exposures and controls for auto, general liability products liability, property and workers compensation. Summarize...
Arch Chicago, IL, USA Full Time
Nationwide
01/30/2026  
Consultant, Loss Control (Human Services)
If you’re passionate about helping people protect what matters most to them at a Fortune 100 company with nearly $70 billion in annual sales, as well as innovating and simplifying processes and operations to provide the best customer value, then Nationwide’s Property and Casualty team could be the place for you! At Nationwide®, “on your side” goes beyond just words. Our customers and partners are at the center of everything we do and we’re looking for associates who are passionate about delivering extraordinary care. Make a Difference with Nationwide At Nationwide, we believe in protecting what matters most—people and communities. Our Human Services Risk Management Team supports organizations that provide care, hope, and essential services to vulnerable populations. By joining us, you’ll play a vital role in helping nonprofits, senior living providers, and community care organizations create safer environments, prevent harm, and strengthen trust . Your expertise will...
Nationwide IL, USA Full Time

 

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