Our underwriters perform a crucial role at Sentry, evaluating prospective customers to determine whether Sentry will offer coverage—and if so, how much—as well as the required premium. This team works with associates across the organization and in nearly every aspect of our business, protecting the company while ensuring our policyholders get fair prices.
We’re committed to providing our Underwriting associates with a rewarding and challenging work environment, as well as opportunities for ongoing professional development and growth.

Across the Sentry Underwriting team, we offer a full range of roles, from entry-level to senior leadership. Here are just a few of the job titles you’ll find here:
Commercial Lines Underwriter
Middle Market Underwriter
National Underwriting Specialist
Territory Underwriting Specialist
Underwriting Specialist
Your skills, experience, and interests may also be a great fit for a role on a different team. Click below to view all available jobs at Sentry.
If you’re a recent graduate or just getting started on your professional pathway, you could have a place at Sentry.