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DevOps Engineer


Sentry Insurance is seeking an experienced IT professional to fulfill a DevOps Engineer position within our Application Platform Services team. In this role, your core responsibilities include researching, installation, maintenance, performance, and support of critical application and data delivery platforms that enable the Company’s IT operations. A significant focus will be on automation of many of the core tasks associated with these responsibilities.

In this position you will have the opportunity to explore a wide variety of technologies and work closely with infrastructure and application teams as well as management across the entire IT organization. Additionally, you will be part of a dedicated team of engineers that sit at the intersection of software engineering and IT infrastructure. If you have a passion for automating application delivery and making Information Technology the best it can be, we want to talk to you!

This position can be filled as a DevOps Engineer or Senior DevOps Engineer based on the selected candidate’s qualifications and experience in our Stevens Point, WI or Middleton, WI office.

What You'll Do

  • Collaborate in a team environment that insists on the highest standards
  • Challenge yourself, your team, and the company to learn and grow with a focus on reaching maximum potential
  • Work closely with teammates to continuously improve solutions focused on providing consistent, reliable, and repeatable levels of service that empower our IT and business partners to deliver highly effective solutions
  • Regularly engage with application development teams to provide technical direction and guidance in automating application and infrastructure deployments
  • Maintain knowledge of and researches application platforms as well as technological advances to effectively address the ongoing demands for enhancements to existing systems and services by participating in internal and external training opportunities
  • Support and enhance Sentry's application delivery solutions (both 3rd party and internally developed)
  • Investigate and aid other infrastructure service areas when troubleshooting service delivery or performance issues

What it Takes

  • Bachelor’s Degree in Computer Science, Engineering, or related discipline or equivalent experience
  • 2+ years of related work experience
  • Experience in at least one major scripting technology (Python, Perl, Powershell, Ruby) and able to leverage these skills to automate repeatable tasks. Coding experience in .NET or Java is a plus
  • Experience administering one or more of the following platforms: RabbitMQ, Elasticsearch, Redis, F5, AWS ALB/ELB or other HTTP load balancers, IIS, Tomcat, Dynatrace, BMC Control-M, Atlassian Products (Jira, Confluence, Bitbucket, Opsgenie)
  • Experience with continuous integration/continuous deployment solutions such as Jenkins, or Infrastructure-as-Code tooling (e.g. Chef, Terraform, CloudFormation)
  • Have knowledge of industry standards and direction and the mindset of a lifelong learner with an eye toward continuous improvement and a desire to innovate
  • Experience in Cloud (AWS) computing is highly desired
  • Strong technical, analytical and communication skills

What You'll Receive

We take great pride in making Forbes’ list of America’s Best Midsize Employers since 2017. A lot of different factors go into that honor, many of which contribute to your job satisfaction.  At Sentry, your total rewards go beyond competitive compensation.  Below are some benefits and perks that you’ll receive.

  • Generous Paid-Time Off plan for you to enjoy time out of the office.
  • 401(K) plan with a dollar for dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future.
  • Group Medical, Dental, Vision and Life insurance to encourage a healthy lifestyle.
  • Pretax Dependent Care and Health Expense Reimbursement Accounts to ease taxes on health spending.
  • Extensive Work-Life Resources to lend a helping hand.
  • Sentry Foundation gift matching program to encourage charitable giving.
  • Continue your education and career development through Sentry University (SentryU).
  • Collaboration, teamwork, and relationships are key at Sentry. To best support our associates and our culture, Sentry is happy to offer flexible work through scheduled work from home days on Mondays and Fridays and in office days Tuesday - Thursday after we return to the office for this position!

How You’ll Apply

If you are interested in joining Sentry’s team, select the one position that you are most interested in being considered for and complete your online application details. If you have applied with us before, you will only need to provide your email address and password. If this is your first time applying, you’ll need to create an account. Please complete your application and upload your resume online.

About Sentry

All of us at Sentry—more than 4,000 associates—have various talents, skills, and backgrounds. We work together to deliver on our promises to our policyholders every day. We’re proud to offer a full line of property, casualty, and life insurance products to help protect businesses, cars, homes, lives, and retirement income.


Our headquarters is in Stevens Point, Wisconsin, with claims and service offices located throughout the United States. From sales to claims, and information technology to marketing, we enjoy a rewarding and challenging work environment with opportunities for ongoing professional development and growth.


Our bright future is built on a long track record of success. We got our start in 1904 and have been helping businesses succeed and protect their futures ever since. Because of the trust placed in us, we’re one of the largest and financially strongest mutual insurance companies in the United States. We’re rated A+ by A.M. Best, the industry's leading rating authority.


Get ready to own your future at Sentry. Opportunities await.

Equal Employment Opportunity

It is our policy that there be no discrimination in employment based on race, color, national origin, religion, sex, disability, age, marital status, or sexual orientation.

Talent Acquisition Specialist

Thank you for your interest in Sentry!

Zach Wierzba

Job Title:
DevOps Engineer
Job ID:
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Madison, WI
Full/Part Time:
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