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Illinois 19
Chicago Full Time underwriter trainee

19 underwriter trainee jobs found in Chicago

Markel
09/26/2026  
Markel 2027 Underwriting Training Program - Central
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 develop skills to review, analyze, accept and decline risks to ensure profitability for Markel. Communicate with underwriting management, product line leaders, colleagues, data analysts, and current and proposed producers. Become familiar with and execute upon underwriting guidelines, policies and procedures. Additionally trainees will be exposed to data analytics and digital technologies that focus on the future of underwriting in the insurance industry. Upon...
Markel Chicago, IL Full Time
Ryan Specialty
09/22/2026  
Underwriting Associate - Commercial Property
Position Summary Velocity Risk is seeking an early-career insurance professional to join our Property Underwriting team in Chicago. This opportunity is well suited for an Underwriting Assistant looking to build toward an underwriting career, a recent college graduate interested in commercial property insurance, or an early-career underwriter with approximately 1–2 years of property underwriting experience. In this role, you will work closely with experienced underwriters to evaluate property risks, support new and renewal business, prepare accounts for underwriting review, and develop an understanding of risk selection, pricing, coverage, and Velocity’s underwriting appetite. The position offers hands-on exposure to the underwriting process and the opportunity to take on increasing underwriting responsibility as your knowledge and experience grow. This position requires the ability to work a hybrid schedule from our Wacker Drive office in downtown Chicago. What will your...
Ryan Specialty Chicago, IL Full Time
UFG Insurance
08/05/2026  
Surety Underwriter
UFG is hiring for a Surety Underwriter who will actively working towards building and maintaining a profitable mix of new and existing surety business by developing and maintaining strong working relationships with the agency force.   Demonstrate strong analytical skills to evaluate risks for acceptability within their authority and company underwriting parameters.  Make regular agency visits and calls to assess growth and profitability of agents in their territory.  Prospect and appoint new quality agents in the territory.  Visit current and potential contractor’s place of business to better assess acceptability and quality of the accounts.  **The ideal candidate will reside in Chicago, Illinois/Greater Chicago area or the Milwaukee, Wisconsin territory** Essential Duties and Responsibilities:   Underwrite new submissions and existing accounts utilizing authority granted by head of Surety and with assistance from mentors. Evaluate and assess financial...
UFG Insurance Chicago, IL Full Time
Ryan Specialty
09/23/2026  
Senior Director Catastrophe Risk
Position Summary The Senior Director of Catastrophe Modeling leads catastrophe risk analytics for Ryan Alternative Risks, an Alternative Risk Transfer (ART) organization built around parametric structures, facultative and treaty reinsurance, and multi-year contracts. This is a distinct discipline from traditional portfolio cat modeling, and the role offers an experienced modeler the chance to apply deep technical skill to novel, structurally complex risk. The Senior Director sits at the intersection of modeling science, data engineering, and underwriting strategy, owning both the technical execution of cat modeling (RMS, AIR) and the tooling, pipelines, and automation that make that modeling fast, accurate, and scalable — while building and managing the team that delivers it. The Senior Director translates portfolio-level model output into underwriting guidance, sets technical standards for the function, and represents catastrophe risk analytics to underwriting and executive...
Ryan Specialty Chicago, IL Full Time
CNA
09/23/2026  
Underwriting Director - Cyber/E&O - Midwest
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.  Leads and directs an underwriting group and is accountable for business results through overall management, profitability, and business development of a book of Cyber/E&O business throughout the Midwest. In conjunction with senior management, works within the highest limits of authority. Has regional, industry, segment, or company-wide scope of responsibility. JOB DESCRIPTION: Essential Duties & Responsibilities Performs a combination of duties in accordance with departmental guidelines: Directs the work activities and has full management responsibility for the performance and development of subordinate staff in accordance with corporate strategic direction. Onboards,...
CNA Chicago, IL Full Time
Westfield
09/22/2026  
2027 Summer Intern Program- Underwriting Intern, Chicago
The Westfield Specialty Intern Program is a paid, ten-week program that offers students the opportunity to obtain firsthand insight into the insurance business.  Every day you'll learn and develop your skills but you'll also have a clear and supportive path ahead of you. You'll gain the confidence to take on real projects, build your network and learn from senior leaders across our business.  The 2027 Summer Intern Program will run from June 7th to August 13th.     Program Elements Include: Classroom and On The Job Training  Weekly Lunch and Learn Series with Senior Leaders Formal Mentor Program  Presentations from Major Brokerage Partners  Teambuilding and Social Activities; including Community Service Event Industry based Group Project    Participants in the Westfield Specialty Summer Intern Program are immersed in the day-to-day operations of a fast-moving, growing insurance company. You will gain valuable, hands-on experience and insurance...
Westfield Chicago, IL Full Time
CNA
09/22/2026  
Underwriting Associate (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.  Under broad supervision, responsible for underwriting risk for the underwriting lifecycle from submission through policy issuance, for both renewal and new business within limited authority. Partnering with Underwriters on all aspects of the Underwriting function including: providing the necessary information to allow for UW to make prudent underwriting decisions. JOB DESCRIPTION: Performs a combination of duties in accordance with departmental guidelines: 1. Performs underwriting analysis and documentation to determine acceptability of risk in accordance with company guidelines and standards for renewal and new business  within assigned Letter of Underwriting Authority. 2.  Handles...
CNA Chicago, IL Full Time
Liberty Mutual
09/15/2026  
Executive Underwriter, Property
Description We are seeking an Executive Underwriter to manage and maintain a significant portion of our Major Accounts Property portfolio in the Central Region. In this role, you will be responsible for handling complex monoline Property accounts with minimum TIVs of $100m, analyzing the customer's property exposures, hazards, financial information, requested coverages, loss history, pricing targets and desired program structure to select business and determine appropriate terms and conditions. Will work closely with Risk Engineering to produce and manage a profitable book of business and manage producer/customer relationships. Maintains the highest level of skills/knowledge in the large property space with average account annual premium of around $1m. Shares underwriting expertise with other underwriters and stakeholders across all levels.   Responsibilities Manages portfolio of brokers/agents & clients. Leverages market presence and expertise to...
Liberty Mutual Chicago, IL Full Time
UFG Insurance
09/11/2026  
Sr Production Underwriter
UFG is looking for a  Sr. Production Underwriter  to join our Great Lakes Region in a multi-line, multi-industry opportunity.  In this role you will be responsible for attracting and underwriting middle market business, deploying effective account management while fostering strong working relationships with agency partners. This role executes underwriting strategy to achieve profit and premium plans. The Sr. Production Underwriter will handle a renewal book in their territory as assigned. This role assists with the resolution of escalated issues, and mentors and coaches team members. While this is a remote work opportunity, the ideal candidate should reside in the Chicago metropolitan area. Responsibilities:   Profitably underwrite complex new and renewal business through risk selection, pricing, contractual integrity, and account management, in accordance with delegated authority, and ensuring regulatory compliance. Demonstrate critical thinking in assessing the...
UFG Insurance Chicago, IL Full Time
CNA
09/04/2026  
Underwriting Associate(Commercial Construction P&C)
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.  Under broad supervision, responsible for underwriting risk for the underwriting lifecycle from submission through policy issuance, for both renewal and new business within limited authority. Partnering with Underwriters on all aspects of the Underwriting function including: providing the necessary information to allow for UW to make prudent underwriting decisions. JOB DESCRIPTION: Performs a combination of duties in accordance with departmental guidelines: 1. Performs underwriting analysis and documentation to determine acceptability of risk in accordance with company guidelines and standards for renewal and new business  within assigned Letter of Underwriting Authority. 2.  Handles...
CNA Chicago, IL Full Time
CNA
09/02/2026  
Underwriting Associate (Technology P&C)
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.  Under broad supervision, responsible for underwriting risk for the underwriting lifecycle from submission through policy issuance, for both renewal and new business within limited authority. Partnering with Underwriters on all aspects of the Underwriting function including: providing the necessary information to allow for UW to make prudent underwriting decisions. JOB DESCRIPTION: Performs a combination of duties in accordance with departmental guidelines: 1. Performs underwriting analysis and documentation to determine acceptability of risk in accordance with company guidelines and standards for renewal and new business  within assigned Letter of Underwriting Authority. 2.  Handles...
CNA Chicago, IL Full Time
AIG
08/29/2026  
Senior Underwriting Assistant
The Senior Underwriting Assistant is an individual contributor within the Underwriting Support Unit of the unit’s field operations.  This role assists the underwriters by screening risk offerings and with pre and post-binding processes. The role also performs services including problem-solving or research projects requiring broad insurance and/or procedural knowledge and works under direct supervision. This role will work on our AIG Captives business line. In addition to the traditional UA duties, this role will: Support regional UA Manager in overseeing all daily business activities and act as the first point of call for all UAs in the region Review new submissions against prescribed criteria to determine if risk qualifies for LOB risk appetite.  Triages submission for missing information and follows up with the broker for outstanding items. Performs a comparison of renewal submission information against prior year information and documents differences for...
AIG Chicago, IL Full Time
Dual North American - Howden Group Holdings
08/29/2026  
AVP/VP Underwriting Builders Risk
At DUAL North America, our core values dictate how we live and work. We are a group with independence and people at its heart and we are a home for talent with a unique culture: the biggest small company in the world. The focus on being a People First business has always been at the very heart of the Group; Our vision was to create an independent business with a unique culture and one that would survive and thrive as a business controlled by the people working for it. And finding the most talented and entrepreneurial people to join the Group has been and will continue to be key. DUAL North America, Inc. is seeking a AVP/VP Underwriting Builders Risk Classification: Exempt/Full-time Reports to: SVP Underwriting or above Travel: Up to 30% or more Salary: $140,000.00- $200,000.00 Role overview DUAL North America is seeking an AVP/VP Underwriter for the Builders Risk division.    At DUAL, AVP/VP Underwriters play a critical leadership role in defining the...
Dual North American - Howden Group Holdings 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
Liberty Mutual
07/29/2026  
Executive Underwriter, Inland Marine
Description The Executive Underwriter will grow and develop a book of complex construction-focused inland marine risks—from builders risk and installation projects to contractors’ equipment and large-scale infrastructure developments. Applies deep technical judgment, market insight, and data-driven analysis to evaluate project exposures, select profitable business, and develop appropriate coverage, terms, conditions, deductibles, limits, and pricing within established underwriting authority. For the most complex, unusual, or high-line-size accounts, partners with senior leaders and internal experts to develop creative, disciplined solutions that protect Liberty Mutual’s portfolio while supporting the success of construction clients. Responsibilities Underwrite and manage construction-focused business:  Evaluate builders risk, installation, contractors’ equipment, project cargo, and infrastructure accounts, considering project scope, construction type,...
Liberty Mutual 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
AIG
06/18/2026  
Regional Production Specialist Sr, Excess & Surplus Lines
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...
AIG Chicago, IL Full Time
AIG
05/14/2026  
Head of Actuarial Pricing Analytics - North America
Head of Actuarial Pricing Analytics - North America At AIG, we are reimagining the way we help customers to manage risk. Join us as a Head of Actuarial Pricing Analytics - North America 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 The Modelling & Advanced Analytics team, within Actuarial - Global Pricing, support the broader global Actuarial function in calibrating commercial lines rating solutions through predictive modelling and market insights. The raters are used by underwriters...
AIG Chicago, IL Full Time
H.W. Kaufman Group
02/27/2026  
Commercial Lines Underwriter
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

 

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