Middle Market Underwriter

Our Underwriters within Sentry's Regional unit work closely with independent agents to underwrite, price and program individual policies/accounts.At Sentry, our business is built around people. And we pride ourselves on the promise to deliver efficient and effective services.  We are currently seeking a result driven individual to fulfill a critical part in underwriting of policies.  As one of our premier Underwriters, you'll be part of a team that stimulates production through independent agencies and then reviews insurance applications and evaluates their potential risk to Sentry.Based on the qualifications and experience of the selected candidate, this position can be filled as an Underwriter Senior, Underwriter Specialist, or Underwriter Specialist Senior.What You'll DoAs a Middle Market Underwriter, you will:Underwrite middle market multi-line accounts with premiums generally in the 50K to 500K range.Be able to thrive in a team environment. Provide feedback to agency teams and underwriting management regarding trends and issues within your assigned territory and provide suggested solutions.Work with other business functions to ensure service and quality objectives are metDemonstrate an understanding of the insurance marketplace and emerging industry issuesComplete assigned project work requiring a high level of technical knowledgePerform other job-related duties including training, presenting, attending sales meetings, traveling to agents, participating in audits, and covering desks for other UnderwritersWhat it Takes Bachelor's Degree or equivalent work experience2-7+ years of work experience underwriting accounts in the following Industries: Construction, Manufacturing, Wholesale, Retail, and Services.Previous Commercial Multi-Line Property Casualty insurance underwriting experienceCompleted insurance courses such as IIA and/or CPCU preferredDemonstrated knowledge of commercial multi-line product line insurance concepts and terminologyExcellent analytical, human relations and communication skillsAbility to meet limited travel requirementsWhat You'll Receive At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that you'll 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.Generous Paid-Time Off plan for you to enjoy time out of the office.401(K) plan with a dollar for dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future.Group Medical, Dental, Vision and Life insurance to encourage a healthy lifestyle.Extensive Work-Life Resources to lend a helping hand.Sentry Foundation gift matching program to encourage charitable giving.Continue your education and career development through Sentry University (SentryU).About SentryWe take great pride in making Forbes' list of America's Best Midsize Employers since 2017. 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, we're one of the largest and financially strongest mutual insurance companies in the United States. We're 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!Joe LarsenJoe.Larsen@ Equal Employment OpportunitySentry 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.

Created: 2026-03-11