Working at Sentry | Glassdoor

Sentry Overview

Stevens Point, WI
1001 to 5000 employees
Company - Private
Insurance Carriers
$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, which is why we’re proud to be ranked as a Forbes Best Midsize Employer. 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. Our culture is just one of the reasons we’re ranked as a Forbes Best Midsize Employer. 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, a 2017 Forbes Best Midsize Employer.

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, a 2017 Forbes Best Midsize Employer.

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

Rating TrendsRating Trends
Recommend to a friend
Approve of CEO
Sentry Chairman of the Board, President and CEO Pete G. McPartland
Pete G. McPartland
99 Ratings
  • Helpful (1)

    "Mostly fine."

    • Work/Life Balance
    • Culture & Values
    • Career Opportunities
    • Comp & Benefits
    • Senior Management
    Current Employee - Claims Specialist
    Current Employee - Claims Specialist
    Neutral Outlook
    Approves of CEO

    I have been working at Sentry full-time (More than 5 years)


    Good PTO right off the bat. Co-workers tend to be pretty cool and local management is also quite good. They are also pretty good when it comes to getting designations.


    There is a tendency in at the director level to be really reactionary and rather than working on issues while getting all sides of the story instead immediately looking to blame someone.

    Advice to Management

    You don't have to blindly back someone, but consider sometimes the customer is wrong, or at least that there is more to the story.

See All 240 Reviews

Sentry Photos

Sentry photo of: Wellness Center Equipment
Sentry photo of: Wellness Center Equipment
Sentry photo of: Wellness Center Equipment
Sentry photo of: Wellness Center Equipment
Sentry photo of: Wellness Center
Sentry photo of: SHO Commons
See All PhotosSee All

Sentry Interviews



Getting an Interview

Getting an Interview




  1. Helpful (1)  

    HR Business Partner Interview

    Anonymous Interview Candidate
    No Offer
    Negative Experience
    Difficult Interview


    I applied online. I interviewed at Sentry.


    Video interview with written questions (not with a live person). The questions asked were:
    1) Not relative to effectively assessing my knowledge, skills, and abilities.
    2) Not related to the job duties posted or
    3) Reflected such a bad culture that I would not want to work there.

    While this company does a a lot of self promotion for enticing applicants to WI, the interview questions left a poor impression of the company.

    Interview Questions

    • Describe a strategy that failed for reasons beyond your control.   Answer Question
See All 62 Interviews

Sentry Awards & Accolades

  • Fortune 500, Fortune, 2015

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