Underwriting Specialist - Middle Market
- Salary
- $90.6K–$136KUSD per year
- Hiring from
- United States
- Work type
- Hybrid
- Posted
- Sep 29, 2026
Based on qualifications and experience, this position can be filled at either an Underwriting Specialist or Senior Underwriting Specialist level.
What You’ll Do
In this role, you will:
- Work closely with agency partners and internal sales partners to obtain information needed to properly underwrite, price, and program individual policies/accounts.
- Through the use of manuals, established procedures, and information collected works on the more complex underwriting assignments. Refer business outside of authority limit.
- Responsible for underwriting of the more complex, larger accounts.
- Evaluate established procedures for effectiveness and recommends change.
- Work closely with other business products functions to ensure service and quality objectives are met. These units include rating, general services, audit, safety sciences, customer accounting and customer service.
- Demonstrate an understanding of the insurance marketplace, and emerging industry issues.
- Train other underwriters, give presentations and conduct training on underwriting procedures.
What it Takes
- Bachelor’s degree or equivalent work experience
- 5+ years of related work experience
- Previous insurance underwriting experience, middle market underwriting experience in construction, manufacturing, wholesale, real estate, and service industries is preferred
- Completion or in the process of taking insurance courses such as IIA and CPCU preferred
- Demonstrated knowledge of specific product line insurance concepts and terminology
- Comprehensive knowledge of reinsurance procedures
- Effective analytical, human relations, and communication skills
- Limited Travel
- In the state of Colorado, as an Underwriting Specialist, the range for annual compensation is between $90,600 - $136,000, based on qualifications and experience.
- In the state of Colorado, as an Underwriting Specialist Senior, the range for annual compensation is between $109,700 - $164,500, based on qualifications and experience.
Here is what you can look forward to as part of our team:
At Sentry, your total rewards go beyond competitive compensation. We’re committed to supporting the whole you, which is why we offer a comprehensive package designed to help you thrive both professionally and personally.
- Hybrid Flexibility: Enjoy the best of both worlds. With optional work from home on Mondays and Fridays and join your team in the office Tuesday through Thursday to collaborate and learn. We provide the technology and tools you need for both your office and home workspace from day one.
- Dining on Us: Depending on your location, we may provide a stipend that can be used at our on-site cafeteria or a meal allowance to keep you fueled.
- Continuous Learning: Unlock your potential through Sentry University and take advantage of our tuition reimbursement program.
- Comprehensive Benefits: We support your whole self with group medical, dental, and vision insurance along with parental leave, pet insurance, caregiver leave, and wellness resources. Options for HSA, FSA, and Dependent Care FSA are available.
- Work-Life Balance: Enjoy your generous Paid Time Off allowance to rest and take advantage of paid Volunteer Time Off to support your community.
- Investing in Your Future: We’re committed to your long-term financial well-being. We offer a 100% company match on the first 8% you contribute to your 401(k) each pay period, and those funds vest immediately.
- Giving Back: Through the Sentry Foundation, we’re proud to support the United Way and make a difference in our communities.
Why Join Sentry?
At Sentry, we believe our people are the heart of our success. We’re proud to be recognized for the culture we’ve built, earning spots on Forbes’ lists for America’s Best Midsize Employers and Best Employers for New Grads, as well as Newsweek’s America’s Greatest Workplaces for Women and Diversity. These honors reflect our commitment to your professional satisfaction and growth.
Building on a Legacy
Our future is bright, but it’s anchored in a long history of stability. Since our founding in 1904, we’ve dedicated ourselves to helping businesses protect their futures. That trust has made us one of the largest and most financially stable mutual insurance companies in the U.S. We’re proud to have maintained an A+ rating from A.M. Best, the industry’s leading authority, for over 30 years.
Your Career, Our Community
Whether you’re working at our headquarters in Stevens Point, Wisconsin, or one of our many offices across the country, you’ll find a challenging and rewarding environment. Explore the Our Teams tab on our Career Page to see the diverse career paths we offer, with a focus on ongoing development and professional growth.
Ready to own your future? Join us at Sentry, opportunities await!
Joe Larsen
Senior Talent Acquisition Specialist
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.
About Us
Our associates are the most important part of our company.
We became one of the most financially strong mutual insurance companies in the U.S. by striving to provide the best possible service to our business customers. We do this by having conversations, forming relationships, and getting to know the people we work with and their businesses.
We make that same commitment to our associates. When you join Sentry, we don’t just want you to perform tasks each day. We want you to enjoy your time with us. You’re in the driver’s seat of your career path here—sharing feedback, creating goals, accessing professional development resources, and identifying how you can contribute to both your success and the success of the company.
Yes, we work hard. But we work with the purpose of helping others, and with the understanding that there’s more to life than work. We invite you to learn more about us. You’ll find we’re much more than insurance.