Career at Sentry
Wherever you are in your career journey, you can enjoy an array of rewarding opportunities at Sentry. We offer positions within Customer Support, Claims, Information Technology, Underwriting, Sales Finance, Actuary, Human Resources, Marketing and more—many of which don’t require you to have previous experience in insurance.
Who we are
Our associates are essential to our long-standing stability and success—so we provide resources to help you grow professionally and personally. Learn more about us.
What We Offer
At Sentry, your Total Rewards package goes beyond competitive compensation and generous paid time off. We provide benefits that focus on the whole person.
Benefits you know and expect
- Medical*
- Dental*
- Vision*
- Disability*
- Life insurance*
- Parental leave*
- Reimbursement accounts: Health Savings Account and Flexible Spending Account*
- Company-paid group life and long-term disability*
- Hybrid work model (not applicable to all associates)
Benefits with your future in mind
- 401(k) plan with an 8% dollar-for-dollar match and immediate vesting*
- Tuition reimbursement program*
- Scholarships programs for dependents of Sentry associates*
- Sentry Credit Union, a full-service financial institution with more than 5,000 shared branches nationwide
Health and wellness
- On-site wellness centers in select offices
- Fit Funding reimbursement of gym memberships for associates at other locations
- Ongoing health and wellness incentives and program
- Sentry Work/Life Resources—provides assistance in areas such as finances, caring for elderly parents, and mental well-being
Growth opportunities
- Sentry University (SentryU): Offers continuing education and career development opportunities
- LinkedIn Learning: An on-demand learning resource where associates have access to thousands of online educational tools
- Designations: Associates can increase their insurance acumen and grow professionally through our numerous designation program options
- Personal development: We also offer opportunities to learn a new skill that doesn’t involve work, such as cooking classes
Community Minded
Supporting the communities where we live and work
Sentry believes contributing time, effort, and resource to its surrounding communities—and supporting associates in their individual efforts to do the same—is an essential part of who we are. Here are some benefits and initiatives from Sentry that highlight our dedication to community support:
Volunteer time off
Our Total Rewards benefits package includes volunteer time off (VTO). The goal is to support volunteer activities that lift up our communities.
United Way campaign
In each of the past several years, we’ve raised more than $1 million for the non-profit organization across our locations. That includes associate donations through pledges, fundraising efforts, and numerous activities held during a two-week campaign every fall—along with a corporate matching contribution by the Sentry Insurance Foundation.
Matching gift program
Through the Sentry Insurance Foundation matching gift program, we match associate and retiree donations to eligible organizations on a 1:1 basis, from $25–$7,500 per associate per year.
Further support of students and our communities
Since 2009, the Sentry Insurance Foundation has donated $16.7 million to boost technology in public and private school districts in our home base of Stevens Point, Wisconsin. That includes a recent $1.7 million grant.

Sentry Insurance
In 1904, members of the Wisconsin Retail Hardware Association gave us our start when they formed their own mutual insurance company. We’ve grown far beyond Wisconsin and the hardware industry in the years since. But we’ve always retained our core values as a mutual company.
We’ve never forgotten our Midwest roots, either. Our true strength comes from our dedication to personalized care—something we’ve provided since our inception. We grew by leveraging knowledge in one market to branch out into similar industries.
We work hard to understand our customers’ businesses—and their industries—inside and out, and we work hard to build long-term relationships. Our current mix of customers is a testament to our broad knowledge. And we put that knowledge into practical use to serve our customers better, offering services to minimize risks in the workplace and providing assistance when something unfortunate happens.
Today, we’re part one of the largest and most financially secure mutual insurance groups in the U.S. We hold this position largely in part to our dedicated associates. Our 5,000 associates bring together their diverse backgrounds, experiences, and skill sets to make Sentry the strong company we are today.
We’re known for our high retention rate, community support, and personal and professional growth opportunities. Learn more about us—and what we can offer you
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