Workplace Technology Engineer (Hybrid Work Model)

We are seeking a Workplace Technology Engineer to join our team and play a key role in supporting and evolving our workplace technology ecosystem.

This position will focus primarily on the Microsoft 365 platform, including Exchange, SharePoint, and Teams, which are foundational to our communication, collaboration, and productivity environment. This position is eligible to work on a hybrid basis out of Sentry's Stevens Point, WI or Madison, WI office locations.

At Sentry, we’re more than just insurance—and we can offer you more than just a job. We want you to enjoy a career with us, where you’re in the driver’s seat of your career path with access to resources to help you succeed personally and professionally.

What You’ll Do

You’ll be a valuable contributor to our team. As a Sentry associate, we believe in your skills and knowledge. Your input and participation matters. You’ll have the opportunity to:

• Innovate: Through our agile development process, you’ll have the opportunity to apply your creativity and innovation to drive new solutions.

• Learn: Sentry provides several resources to help you further your career and continue your personal development, including Sentry University, LinkedIn Learning, and peer-led educational sessions and communities.

• Grow: Sentry provides many opportunities to grow in your career. Through meaningful, ongoing conversations around growth and development, we encourage all associates to take ownership in their career path.

• Contribute: As a Workplace Technology Engineer, you will:

  • Administer, support, and enhance workplace collaboration technologies with a primary focus on Microsoft 365, including Exchange, SharePoint, and Teams.

  • Provide engineering and operational support for workplace technologies, ensuring reliability, performance, and a high-quality user experience.

  • Troubleshoot and resolve complex technical issues across collaboration platforms, messaging systems, integrations, and end-user technologies.

  • Serve as an escalation point for difficult or recurring issues that require deeper technical analysis and cross-functional coordination.

  • Design, develop, and maintain PowerShell scripts and automation workflows to streamline administration, reduce manual effort, and improve consistency.

  • Leverage automation tools such as Jenkins to support job scheduling, workflow execution, and operational efficiency where appropriate.

  • Partner with infrastructure, security, support, and business teams to implement improvements and solve technology challenges.

  • Create and maintain technical documentation, standard operating procedures, support articles, and knowledge base content for workplace technologies.

  • Establish repeatable processes and operational standards that improve service quality and reduce support friction.

  • Mentor and enable support teams by providing technical guidance, troubleshooting frameworks, and documentation to strengthen break/fix support for associates.

  • Identify opportunities for platform optimization, service improvements, and automation-driven innovation.

  • Participate in testing, change implementation, and rollout planning for new features, updates, and technology solutions.

  • Monitor platform health, identify trends, and proactively address risks or recurring issues before they impact users.

• What it Takes:

  • Bachelors Degree in Information Technology or equivalent related work experience.

  • Minimum of 2 years of related work experience.

  • Experience with operating systems and Microsoft 365 ecosystems. Specifically Exchange, SharePoint, and Teams.

  • Proficient with scripted automation in PowerShell.

  • Strong knowledge of infrastructure technology.

• Preferred Skills:

  • Strong understanding of service operations, incident response, and root cause analysis.

  • Experience developing scalable support models and improving tiered support effectiveness.

  • Ability to identify repetitive tasks and convert them into automated solutions.

  • Knowledge of end-user collaboration tools and technologies that impact workplace productivity.

  • Strong documentation discipline and commitment to operational excellence.

  • Customer-focused mindset with a passion for improving the associate technology experience.

If you have experience in the skills listed above, please consider joining our Sentry team!

What You’ll Receive

You can enjoy a complete benefits package, including generous paid time off, 8% 401(k) match, matching charitable gift program, bonus plan based on company performance, meal stipends, associate discounts, volunteer time off and more!

You want a positive work/life balance. Our hybrid work model allows you to enjoy the benefits of working from home on Monday and Friday, but also provides the opportunity for team building and collaboration when working in the office on Tuesday, Wednesday, and Thursday. To help you work effectively and comfortably in both locations, we provide you with equipment to work at home and in the office.

About Sentry

Our Background: We’re part of one of the largest and most financially secure mutual insurance groups in the nation. We’ve earned an A+ rating from AM Best every year since 1992. Our associates bring together diverse backgrounds, experiences, and skillsets to make Sentry who we are. We’re honored to earn a spot on Forbes list of America's Best Midsize Employers, joining a select group of 400 companies. We’re in the business of helping others, and that includes the communities where we live and work. Our annual United Way campaign has raised more than $1 million for the past several years.  

Our Stevens Point campus offers a full-service fitness center, swimming pool, basketball and racquetball courts, auto center, credit union, on-site Aspirus clinic, restaurants, boutique hotel, and the award-winning SentryWorld golf course.

How You’ll Apply

We’d love for you to join us. Please complete your online application and upload your resume on our Careers site. If you have applied with us before, you only need to provide your email address and password. If this is your first time applying with Sentry, please create an account.

If you have specific questions regarding the position, application process, or are interested in learning more about Sentry, please reach out to Katelynne Rivera, Talent Acquisition Specialist Sr.

For this position, Sentry does not offer employment to holders of F-1, J-1, and H-1 Visas.

Get ready to own your future at Sentry. Your opportunity awaits.

Talent Acquisition Specialist

Thank you for your interest in Sentry!

Katelynne Rivera

Katelynne.Rivera@Sentry.com

Equal Employment Opportunity

Sentry is an Equal Opportunity Employer. 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.