M365 Engineer

Position

Lead, Technology Operations - M365 Engineer

Hybrid - Chicago, IL

$105,000-$120,000 annually, eligible for annual bonus for meeting performance goals

Highstreet Insurance Partners (Highstreet) is one of the fastest-growing insurance agencies in the U.S. Founded with the mindset of putting people first, Highstreet brings technical and industry experience together to serve and protect customers while providing its internal teams with the tools and resources to grow. We love to help people pursue life’s opportunities with tenacity and confidence to create stronger, more resilient communities.

We do it for all our futures.

The M365 Engineer is responsible for designing, implementing, supporting, and improving Microsoft 365 collaboration, automation, and productivity solutions across the organization. This role combines hands-on technical delivery with practical project coordination, working closely with business stakeholders, IT teams, and end users to translate requirements into secure, scalable, and user-friendly solutions.

The ideal candidate has strong experience with Microsoft 365 administration, SharePoint Administration, Power Automate workflows, scripting, automation, and practical project coordination, but this role places greater emphasis on delivering broader Microsoft 365 solutions, improving business processes, and supporting modern workplace adoption.

• Assist with the design, configuration, and administrate SharePoint Online sites, lists, libraries, pages, permissions, metadata, and document management structures as part of broader Microsoft 365 solution delivery.
• Support SharePoint migration and consolidation activities, including inventory review, site and content mapping, permissions analysis, migration validation, cleanup, and post-migration support.
• Partner with business teams to gather requirements, assess current processes, and deliver Microsoft 365 solutions that improve collaboration, content management, and workflow efficiency.
• Create, maintain, and troubleshoot Power Automate workflows that support approvals, notifications, task routing, data collection, and business process automation.
• Develop scripts and automation using tools such as Power Shell to support Microsoft 365 administration, reporting, provisioning, migrations, cleanup, and repeatable operational tasks.
• Support Microsoft 365 services including SharePoint Online, Teams, One Drive, Exchange Online, Entra
  -related integrations, and related collaboration tools.
• Assist with planning, coordinating, and executing Microsoft 365 projects, including timelines, task tracking, stakeholder communication, testing, deployment, and post-implementation support.
• Maintain appropriate governance for SharePoint sites, permissions, naming standards, lifecycle management, and information architecture.
• Troubleshoot Microsoft 365 issues, identify root causes, document resolutions, and collaborate with vendors or internal teams when escalation is required.
• Create and maintain technical documentation, user guides, process diagrams, support procedures, and solution design notes.
• Monitor Microsoft 365 roadmap changes, feature releases, and best practices to recommend improvements that enhance productivity, security, and user experience.

• Hands-on experience administering, configuring, or engineering Microsoft 365 services in a business environment.
• Familiarity with SharePoint Online site design and creation, including navigation, permissions, lists, libraries, pages, and document management concepts.
• Experience building, supporting, and troubleshooting Power Automate workflows and business process automations.
• Working knowledge of scripting,…