Workplace Technology Engineer (Hybrid Work Model)

Sentry Insurance Agency•Madison, WI

8d•Hybrid

About The Position

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.

Requirements

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.

Nice To Haves

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.

Responsibilities

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.