Working at Sentry | Glassdoor

Sentry Overview
Stevens Point, WI
1001 to 5000 employees
Company - Private
$2 to $5 billion (USD) per year
At Sentry, we understand what businesses look for in an insurance company. Because we’ve been there ourselves. We got our start in 1904, when members of the Wisconsin Retail Hardware Association formed their own insurance company. But it was the true strength of ... Read more

Sentry – Why Work For Us?

More than insurance.

At Sentry, we truly are more than insurance—we’re driven to serve our customers and our communities. And we couldn’t do it without our hard-working, dedicated associates. Over the past 100-plus years, we’ve delivered on our promise to our policyholders while growing into one of the nation’s largest and strongest mutual insurance companies. Our associates—more than 4,000 strong—may have different talents, skills, and backgrounds, but we all share the same vision and attitude that drive our continued success individually and as an organization.

If you’re a positive, motivated professional, consider owning your future at Sentry and exploring the opportunities that await you. You’ll find more than just a job at Sentry.

History. Community. Charity. Development. Culture is key at Sentry.

At Sentry, we’re more than insurance—and we offer all of our associates more than just a job. Those who join our team become part of a rich, 100-plus year history that expands well beyond a job title. Our associates come together to create a vibrant community. From sponsoring and participating in community events to supporting charities like United Way, Operation Bootstrap, and the Humane Society of Portage County, we take an active role in all of the communities in which we live and work. We’re also committed to providing our associates with opportunities for ongoing professional development and growth.

Own your future with Sentry Insurance.

Sentry is one of the largest and strongest mutual insurance companies in the nation—a position we proudly hold because of the long-standing relationships our dedicated associates have with our policyholders—relationships built on trust, expertise, and superior service. More than 4,000 strong, our associates bring together diverse backgrounds, experiences, and skill sets to make Sentry who we are.

Whether you’re new to the job market, looking to advance your career, or are a seasoned professional, we offer an array of rewarding career opportunities across a variety of functions, from information technology, claims, sales, and underwriting, to marketing, human resources, finance, and more. 

Find more than just a job. We invite you to explore the career opportunities that await you at Sentry.

Experience that can’t be taught in a classroom.

If you’re a hard-working, career-minded student looking for a bright future, a paid internship or co-op program opportunity with Sentry might be the right fit for you. Our student-specific programs provide you with practical experience in real-world, real-work situations.

From internship opportunities in actuarial, claims, finance, human resources, and more, to our industry-leading information technology co-op programs in Madison and Stevens Point, Wisconsin, we offer driven students the chance to gain experience that can’t be taught in a classroom—experience that’ll prove to be invaluable no matter where your future takes you.

We invite you to explore the internship and co-op program opportunities that await you at Sentry.

Real people. Real insight.

What better way to learn about a company than to hear directly from its employees? Hear what real Sentry associates have to say about working as part of our team.

Sentry Reviews

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Sentry Chairman of the Board, President and CEO Pete G. McPartland
Pete G. McPartland
89 Ratings
  • Featured Review

    Helpful (2)

    "Claims Adjuster"

    Star Star Star Star Star
    • Work/Life Balance
    • Culture & Values
    • Career Opportunities
    • Comp & Benefits
    • Senior Management
    Current Employee - Claims Adjuster in Stevens Point, WI
    Current Employee - Claims Adjuster in Stevens Point, WI
    Positive Outlook

    I have been working at Sentry full-time (Less than a year)


    Sentry is a wonderful company with great people. The offer tremendous amenities as well. If you are looking for a new job I would highly recommend Sentry.


    No complaints. Every job has a few things that I am sure every individual would like to change. On the whole, however, there is nothing of substance to complain about.

    Advice to Management

    Please continue doing a wonderful job managing your company and employees. I would not change a thing.

See All 223 Reviews

Sentry Interviews



Getting an Interview

Getting an Interview





    Safety Consultant Interview

    Anonymous Interview Candidate
    No Offer
    Neutral Experience
    Average Interview


    The process took 4+ weeks. I interviewed at Sentry.


    The interview process was interesting. I applied online and then was scheduled for a video interview. The first interview went fine and then I had another video interview with the head safety consultant out of Wisconsin. I received an e-mail the next week saying I didn't get the job. In my opinion, I was already making too much money and the company couldn't offer me more. The position seemed like a lot of hours and I couldn't get a direct answer on how many hours a week I would work. The position was for the Southern California area and I would be the only risk rep for that area (limited support). I didn't get an offer, but probably would have turned it down due to the amount of hours and amount of unknowns.

    Interview Questions

    • Explain a time you were in a difficult situation at work and how you handled it.   1 Answer
See All 47 Interviews

Sentry Awards & Accolades

  • Fortune 500, Fortune, 2015

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