23 middle market jobs found in Chicago

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: CNA’s Commercial Middle Markets team provides standard lines commercial property and casualty insurance products such as General Liability, Property, Inland Marine, Commercial Auto, Workers' Compensation, and Umbrella to businesses of all sizes. Our Middle Markets team underwrites a diverse mix of business and industry classes including Manufacturing, Professional Services, Financial Institutions, Real-estate, Distributors, Technology, Wholesale, and Retail. Typical account sizes range from $75,000 up to $2,000,000 and over in premium on a multi-line basis. The UA Manager manages a staff of Underwriting Associates across multiple geographies, lines of business,...

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...

The Senior Middle Market Broker provides knowledge, leadership, insight, and direction for broking activities to ensure that clients’ expectations are regularly met. This role incorporates a wide level of expertise but always assumes the broker is capable of handling accounts independently. The size and complexity of the account can vary. More experienced brokers may be responsible for training and supervising associate brokers. Responsible for ensuring that relevant regulatory and technical standards are met. Helps drive the broking team to achieve agreed operational and financial goals and objectives.   Note: Visa employment-based non-immigrant visa sponsorship and/or assistance is not offered for this specific job opportunity. The Role Orchestrate new business placement, renewals, and alterations of existing coverage Develop, review, and deliver presentations to secure new and build on existing relationships Review and evaluate information and analytics to assess and...

Come join our team! There are many reasons why EPIC Insurance Brokers & Consultants has become one of the fastest-growing firms in the insurance industry. Fueled and driven by capable, committed people who share common beliefs and values and “bring it” every day, EPIC is always looking for people who have “the right stuff” – people who know what they want and aren’t afraid to make it happen. Headquartered in New York City and founded in 2007, our company has over 4,000 employees nationwide. With locations spread out across the U.S., our local market knowledge and industry expertise helps support our clients' regional and global needs. We have grown very quickly since our founding, and we continue to see growth and success thanks to our hard-working and growth-minded employees.  Our core values are: Owner mindset, Inspire trust, Think big, and Drive results. If these values and growth align with what you're looking for in your next career? Then consider joining our...

Job Type: Permanent Build a brilliant future with Hiscox   Join our dynamic and forward-thinking Claims team! Here, you’ll be part of an energetic and innovative group, with the chance to help shape insurance products and collaborate with business leaders throughout the organization. **Please Note: This position is primarily hybrid and requires in-office attendance at least two (2) days per week for candidates that are located near one of our office locations. However, qualified remote candidates will also be considered ** The Position Can Be Based In: Atlanta, GA Boston, MA Chicago, IL Manhattan, NY West Hartford, CT Our Complex Claims Specialist-Miscellaneous Professional Liability role is an individual contributor responsible for the handling of mid to high-severity primary Miscellaneous Professional Liability claims for the organization from inception to resolution.  This includes, but is not limited to, insurance agents, property...

Company Details From middle market to Fortune 500 companies, Berkley Custom’s team is committed to providing excellent service and a consistent approach to meet the needs of their brokers and their customers, bringing specific expertise in excess casualty as well as a variety of targeted primary and excess programs.   They seek to outperform competitors with focus and deep understanding of their client’s priorities and by developing creative risk solutions to meet their long-term needs. Their key differentiators include the following: EXCLUSIVE PARTNERSHIPS – Berkley Custom works exclusively the wholesale brokerage community as well as their program partners, and continually builds upon long established relationships with a passion for superior service for their appointed producers. INDUSTRY PROFESSIONALS  – Berkley Custom attracts and retains professionals with significant experience in their field, many with over 25 years in the business....

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 600 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 that...

Job Type: Permanent Build a brilliant future with Hiscox   VP, Practice Leader – Cyber & Tech E&O Reports to: SVP, Head of Professional Lines Underwriting Location: NYC, Atlanta, Chicago, Hartford, Boston Band: III Travel: Up to 25%   Team: Works closely with cross-functional stakeholders including all distribution channels, 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 all Hiscox USA channel 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...

Job Type: Permanent Build a brilliant future with Hiscox   VP, Practice Leader – Management Liability Reports to: SVP, Head of Professional Lines Underwriting Location: NYC, Atlanta, Chicago, Hartford, Boston Band: III Travel: Up to 25%   Team: Works closely with cross-functional stakeholders including all distribution channels, marketing, distribution development, claims, actuarial, underwriting operations, as well as the CUO org. Role Overview: The VP, Practice Leader – Management Liability is a strategically critical leader responsible for driving profitable growth and technical excellence across all Hiscox USA channel 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 change...

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.  The Senior Product Owner serves as the customer proxy to the Agile team within the agile process and is the final authority for decisions regarding priority, business value, and functionality for all the work done by the Agile development team. The Senior Product Owner has the ability to analyze complex cross functional business processes and define integrated user stories using industry standard techniques and is able to apply modified approaches and techniques to meet different circumstances. In partnership with their Scrum Master, the Senior Product Owner will monitor metrics and suggest new ways of increasing quality and verify the business value delivered by the team. The Senior Product...

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.   Depending on experience, we are considered candidates for our Senior or Executive-level Underwriting positions.   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...

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...

Job Type: Permanent Build a brilliant future with Hiscox   Put your claims skills to the test and join one of the top Professional Liability Insurers in the Industry as a Complex Claims Specialist!   **Please Note: This position is primarily hybrid and requires in-office attendance at least two (2) days per week for candidates that are located near one of our office locations. However, qualified remote candidates will also be considered** The Position Can Be Based In: Atlanta, GA Boston, MA Chicago, IL Manhattan, NY West Hartford, CT About the Hiscox Claims team:   The US Claims team at Hiscox is a growing group of professionals with experience across private practice and in-house roles, working together to provide the ultimate product we offer to the market. Complex Claims Specialists are empowered to manage their claims with high levels of authority to provide fair and fast resolution of claims for our insured and...

Job Type: Permanent Build a brilliant future with Hiscox   Bring your Passion and Enthusiasm to our Team! We are a fun, innovative and growing Claims team where you’ll get the opportunity to learn multiple insurance products and interact with business leaders across the organization.    **Please Note: This position is primarily hybrid and requires in-office attendance at least two (2) days per week for candidates that are located near one of our office locations. However, qualified remote candidates will also be considered** The Position Can Be Based In: Atlanta, GA Boston, MA Chicago, IL Manhattan, NY Scottsdale, AZ West Hartford, CT                    The Role: The Senior Claims Examiner adjudicates assigned claims within given authority and provides operational support to the claims team. This person also: Adjusts and resolves moderate to complex claims that includes all phases of litigation Accurately...

Job Type: Permanent Build a brilliant future with Hiscox   Bring your Passion and Enthusiasm to our Team! We are a fun, innovative and growing Claims team where you’ll get the opportunity to learn multiple insurance products and interact with business leaders across the organization.    **Please Note: This position is primarily hybrid and requires in-office attendance at least two (2) days per week for candidates that are located near one of our office locations. However, qualified remote candidates will also be considered** The Position Can Be Based In: Atlanta, GA Boston, MA Chicago, IL Manhattan, NY Scottsdale, AZ West Hartford, CT                    The Role: The Senior Claims Examiner adjudicates assigned claims within given authority and provides operational support to the claims team. This person also: Adjusts and resolves moderate to complex claims that includes all phases of litigation...

Description Summary: The Commercial Relationship Mgr III is responsible for building and servicing a sound and profitable portfolio of commercial business relationships and loans, and satisfying and exceeding customer needs and expectations, as well as credit and regulatory requirements, for originating and structuring Commercial loans. Originate, monitor and renew loan relationships consistent with the bank’s policies and procedures. Serves as the point person in determining the customer's needs and meeting them through the seamless delivery of the bank's products, services and associated resources.  Will be assigned a minimum sales goal of $100MM and a minimum portfolio of $60MM in commitments.  Works with the most sophisticated customers and on the  most complex deal structures.  Can mentor more junior Relationship Managers. Duties & Responsibilities: Originate, analyze, structure and close profitable...

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...

Job Description Amazing Career Moments Happen Here   Transforming the insurance industry is ambitious, we know. That’s why at Applied, 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. With 40+ years of experience in the Insurtech game, we’re not just redefining what’s achievable; we’re creating a place where amazing career moments are made possible.    Position Overview We’re searching for a Senior Compensation Analyst to join the People team in a remote or hybrid capacity out of our Chicago office. We’re in the middle of a multi-year compensation roadmap built around high-impact, employee-centric initiatives, and you will be a driving force behind it. As a Senior Compensation Analyst, you’ll own meaningful work...

Job Description ABOUT US At HUB International, we are a team of entrepreneurs. We believe in protecting and supporting the aspirations of individuals, families, and businesses. We help our clients evaluate their risks and develop solutions tailored to their needs. We believe in empowering our employees to learn, grow, and make a difference. Our structure enables our teams to maintain their own unique, regional culture while leveraging support and resources from our corporate centers of excellence. HUB is a global insurance and employee benefits broker, providing a boundaryless array of business insurance, employee benefits, risk services, personal insurance, retirement, and private wealth management products and services. With over $5 billion in revenue and almost 20,000 employees in 600 offices throughout North America, HUB has grown substantially, in part due to our industry leading success in mergers and acquisitions Responsibilities Platform...

ABOUT US At HUB International, we are a team of entrepreneurs. We believe in protecting and supporting the aspirations of individuals, families, and businesses. We help our clients evaluate their risks and develop solutions tailored to their needs. We believe in empowering our employees to learn, grow, and make a difference. Our structure enables our teams to maintain their own unique, regional culture while leveraging support and resources from our corporate centers of excellence. HUB is a global insurance and employee benefits broker, providing a boundaryless array of business insurance, employee benefits, risk services, personal insurance, retirement, and private wealth management products and services. With over $5 billion in revenue and almost 20,000 employees in 600 offices throughout North America, HUB has grown substantially, in part due to our industry leading success in mergers and acquisitions OVERVIEW As a member of the Change Enablement team within the...