Sentry Insurance
InsuranceDirect Workday career site

Underwriting Specialist - Middle Market

Pay
$90,600 – $164,500 per year
Location
Denver, CO · Hybrid
Job type
Full-time
Level
Mid-level
Experience
5+ years
Education
Bachelor's degree
Listed
30 days ago

Skills & highlights for this role

  • commercial insurance underwriting
  • reinsurance procedures
  • policy pricing

Also useful

  • middle market underwriting
  • construction insurance
  • manufacturing insurance

Stated benefits & perks

  • Health
  • Dental
  • Vision
  • 401k match
  • Tuition

About the role

Applies Underwriting policy, philosophy and procedures to evaluate the acceptability of submitted business. Based on qualifications and experience, this position can be filled at either an Underwriting Specialist or Senior Underwriting Specialist level.

Pay and benefits

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!

Read the original posting

From Sentry Insurance's careers page, first listed on Rolev.ai on October 10, 2026. Rolev.ai is not the employer.

How Rolev.ai helps with this application

Rolev.ai is a job search and application tool for US job seekers. For this Underwriting Specialist - Middle Market role at Sentry Insurance, it shows how your resume fits, tailors your resume to the posting, and prepares the application for you to review.

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Common questions

What is the salary for the Underwriting Specialist - Middle Market role at Sentry Insurance?

The Underwriting Specialist - Middle Market posting at Sentry Insurance states compensation of $90,600 – $164,500 per year. It is listed as a full-time position. Final pay may depend on location, experience, and interview evaluation on Sentry Insurance's official career site.

Where is the Underwriting Specialist - Middle Market job at Sentry Insurance located?

This Underwriting Specialist - Middle Market position at Sentry Insurance is located in Denver, CO (Hybrid). Always check Sentry Insurance's application page for specific state eligibility or relocation policies.

What qualifications are required for Underwriting Specialist - Middle Market at Sentry Insurance?

For the Underwriting Specialist - Middle Market role, Sentry Insurance highlights 5+ years of relevant experience; a bachelor's degree; experience with commercial insurance underwriting, reinsurance procedures, policy pricing. Rolev.ai can score your existing resume against these requirements and show any skill gaps before you apply.

How do I apply for the Underwriting Specialist - Middle Market position at Sentry Insurance?

This listing links directly to Sentry Insurance's Workday application page. You can apply directly on Sentry Insurance's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Workday application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.