Renewal Underwriting Executive-National Accounts (Chicago)

Sentry Insurance
Chicago, IL
As a Renewal Underwriting Executive in our National Account business unit, you will provide consistent customized service through professional communication with customers and brokers.

Sentrys dedication to customers is embodied by our best employees. At Sentry, our associates take care of our customers with a passion for service and delivering business results. The primary responsibility is to retain accounts by developing and delivering a comprehensive stewardship process that fosters strong relationships with assigned National Accounts. The Renewal Underwriting Executive applies underwriting policy, philosophy and procedures to evaluate the acceptability of submitted or existing business.

The Renewal Underwriting Executive will serve the Chicago territory and will reside in the Chicago, IL, Madison, WI, Milwaukee, WI or Stevens Point, WI area. If the selected candidate resides in Stevens Point, WI they will report to our Division Street office location.

For candidates located in Illinois, the base salary range for this opportunity is $99,660-$149,600.

What Youll Do

Our Renewal Underwriting Executive within Sentrys Business Products National Accounts unit will lead the underwriting strategy, customer service, and renewal negotiations for an existing book of business while developing and maintaining a positive working relationship with our territory executives, brokers and clients to obtain information needed to properly underwrite, price, and determine program structure of individual policies/accounts.

In addition, youll:

  • At both Sentry Home Office and broker/insured location, present issues and opportunities that affect efficient services, profit and growth opportunities, and the promotion of specific insurance products.

  • Through use of manuals, established procedures, and information collected, work on basic to complex underwriting assignments. Refer business outside of authority limit.

  • Coordinate services between the National Accounts customer, broker, claims, loss control and customer accounting.

  • Work within specific underwriting limits and authority on National Accounts assignments that require technical knowledge and experience.

  • Handle renewal order and initiate renewal processing and billing. Follow up on security and agreement issues.

  • Demonstrate an understanding of the insurance marketplace and emerging industry issues.

  • Be directly involved in solving credit problems with assigned accounts and brokers.

  • Handle day-to-day service issues including retro adjustment and audit questions.

  • Be responsible for developing and delivering a comprehensive Stewardship Reports that will include benchmark targets and results.

  • Encourage the sharing of insurance expertise and foster stronger relationships with customers.

  • Coordinate communication to National Accounts customers on new or enhanced services.

  • Monitor loss control plans and other service plans to ensure that the customer is receiving the services that have been promised. Encourage use of all of Sentrys Risk Management programs by demonstrating cost savings to National Account customers.

  • Maintain privacy and confidentiality requirements as required by legislation.

  • Participate in National Accounts sales meetings.

  • As needed, train other underwriters, facilitate presentations and conduct training on underwriting procedures. Basic reinsurance assignments may be performed.

What it Takes

  • Bachelors degree preferred or equivalent work experience.

  • 2 years Business Products underwriting experience required. National Accounts underwriting experience preferred.

  • Completion of IIA, CEBS, CPCU and LOMA insurance courses/designations preferred.

  • Demonstrated communication skills required to provide excellent external and internal customer service.

  • Ability to obtain and maintain a property and casualty license.

  • Ability to have and maintain an acceptable driving record to meet travel requirements of the job (25% - 30% travel requirement).

What Youll Receive

At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that youll receive.

  • Sentry is happy to offer flexibility through a scheduled Hybrid work model. Monday and Friday work from home if you choose to, Tuesday through Thursday in office.

  • As a Sentry associate, you will have an in-office workspace and materials for your home office. In addition to the laptop you will receive prior to your start, Sentry will provide equipment for your home office.

  • Meal Subsidy available for associates who report to an office.

  • 401(K) plan with a dollar for dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future.

  • Continue your education and career development through Sentry University (SentryU) and utilize our Tuition Reimbursement program.

  • Generous Paid-Time Off plan for you to enjoy time out of the office as well as Volunteer-Time Off.

  • Group Medical, Dental, Vision, Life Insurance, Parental Leave, and our Health and Wellness benefits to encourage a healthy lifestyle.

  • Well-being and Employee Assistance programs.

  • Sentry Foundation gift matching program to encourage charitable giving.

About Sentry

We take great pride in making Forbes list of Americas Best Midsize Employers. A lot of different factors go into that honor, many of which contribute to your job satisfaction.

Our bright future is built on a long track record of success. We got our start in 1904 and have been helping businesses succeed and protect their futures ever since. Because of the trust placed in us, were one of the largest and financially strongest mutual insurance companies in the United States. Were rated A+ by A.M. Best, the industry's leading rating authority.

Our headquarters is in Stevens Point, Wisconsin, with offices located throughout the United States. From sales to claims, and information technology to marketing, we enjoy a rewarding and challenging work environment with opportunities for ongoing professional development and growth.

Get ready to own your future at Sentry. Opportunities await!

Casey Van Der Geest

[email protected]

Equal Employment Opportunity

Sentry is an Equal Opportunity Employer. It is our policy that there be no discrimination in employment based on race, color, national origin, religion, sex, disability, age, marital status, or sexual orientation.

Posted 2026-02-07

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