Sentry earned an A+ rating for the 34th consecutive year.
Careers
About Sentry
Our beginning
We’ve been helping people and businesses protect what matters most since 1904—when members of the Wisconsin Retail Hardware Association formed their own mutual insurance company. While we’ve grown far beyond our Midwest roots, we hold tight to what started it all: a commitment to personalized care, practical expertise, and long-term relationships.
Proven strength and stability
Today, Sentry is one of the largest and most financially secure mutual insurance groups in the country. We offer a wide range of commercial insurance products for businesses across industries, along with direct-to-consumer products through trusted brands like Dairyland and The General.
120+
Years
we’ve been insuring businesses.
$8B
Policy surplus
keeps us among the best-capitalized in the industry.
A+
(superior) rating
by AM Best* every year since 1992.
Built on a foundation of service
Expertise
We deliver individualized care through dedicated teams for specific industries.
Connection
We work to get to know our customers to provide the best possible insurance solutions.
Community
We support our communities through hands-on volunteer work and meaningful giving.
A purpose-driven culture
We believe in doing the right thing—for our customers, our associates, and our communities. That mindset shapes our company culture, where we work with purpose and prioritize personal and professional growth.
Our 6,000 associates nationwide bring together their diverse backgrounds, experiences, and skill sets to make Sentry the organization it is today.
Giving isn’t what we do—it’s who we are
Learn how we support the communities where we live and work.
Brands of Sentry
The Sentry Insurance Group is made up of five distinct brands, each with its own focus and expertise—but all united by a shared commitment to delivering exceptional service and value to our customers. Explore the brands of Sentry and see how, together, we offer our associates a supportive environment, great benefits, and room to grow both professionally and personally.
An award-winning workplace
Our commitment to creating a positive, people-first culture hasn’t gone unnoticed. We’re proud to be recognized for our outstanding workplace culture.
Recognized as one of America’s Greatest Workplaces for Diversity by Newsweek.
Ranked 13th among Wisconsin’s largest private companies by revenue and impact by Deloitte.
Sentry is one of America’s Best Midsize Employers, according to Forbes.
For the second year in a row, Newsweek named Sentry one of America’s Greatest Workplaces for Women.
Forbes names Sentry as one of the Best Employers for new Grads.