M365 Engineer

Highstreet Insurance Partners

Chicago (IL)

On-site

USD 105,000 - 120,000

Full time

14 days+

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Benefits offered by this job

Employer Paid Life & AD&D

Employer Paid Short- & Long-term-disb

Paid Holidays

401k with employer match

Health, Vision, and Dental insurance

Job summary

Highstreet Insurance Partners is seeking a Lead, Technology Operations - M365 Engineer to design, implement, and support Microsoft 365 solutions across the organization. The role emphasizes modern workplace adoption, security, and scalable collaboration tools, with a strong focus on Power Automate, SharePoint Online, and scripting for automation.

The ideal candidate will lead projects, coordinate with stakeholders, and deliver secure, maintainable Microsoft 365 environments.

Qualifications

Hands-on experience administering Microsoft 365 services in a business environment.
Experience with SharePoint Online site design, navigation, permissions, lists, libraries, and document management.
Experience building, supporting, and troubleshooting Power Automate workflows and business process automations.
Ability to automate administrative tasks and produce reporting using scripting (PowerShell).
Practical project management experience including task coordination and stakeholder communication.

Responsibilities

Design, configure, and administer SharePoint Online sites, lists, libraries, and document management structures as part of Microsoft 365 solutions.
Support SharePoint migration and consolidation activities with mapping, permissions analysis, and post-migration support.
Gather requirements with business teams and deliver Microsoft 365 solutions that improve collaboration and workflow efficiency.
Create and maintain Power Automate workflows for approvals, notifications, and data collection.

Skills

Microsoft 365 administration

SharePoint Online

Power Automate workflows

PowerShell scripting

Project coordination

Documentation & communication

Education

Bachelor's degree in IT/CS or related field

Tools

Power Apps

Microsoft Graph

JSON formatting

REST APIs

Job description

Position: Lead, Technology Operations - M365 Engineer

Location: Hybrid - Chicago, IL

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

Company Background

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.

Position Summary

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.

Key Responsibilities

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 PowerShell to support Microsoft 365 administration, reporting, provisioning, migrations, cleanup, and repeatable operational tasks.
Support Microsoft 365 services including SharePoint Online, Teams, OneDrive, Exchange Online, Entra ID-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.

Required Qualifications

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, preferably PowerShell, with the ability to automate administrative tasks and produce useful reporting.
Practical project management experience, including task coordination, stakeholder communication, status tracking, testing, and implementation support.
Ability to translate business requirements into technical solutions that are secure, maintainable, and easy for end users to adopt.
Strong troubleshooting, analytical, documentation, and communication skills.
Ability to work independently, manage multiple priorities, and collaborate effectively with technical and non‑technical teams.

Preferred Qualifications

Experience with Power Apps, Microsoft Graph, JSON formatting, REST APIs, SharePoint Framework, and other Microsoft 365 extensibility tools.
Experience with Microsoft Teams governance, OneDrive administration, Exchange Online administration, or Microsoft Purview features.
Experience supporting migrations, acquisitions, tenant consolidations, or legacy content modernization efforts.
Familiarity with IT service management practices, change management, release management, and production support processes.
Microsoft certifications related to Microsoft 365, Power Platform, Azure, security, or collaboration services.

Core Competencies

Technical problem solving and root‑cause analysis
Business process improvement and workflow automation
Microsoft 365 collaboration tools and information management
Project coordination and stakeholder management
Security‑minded solution design
Clear documentation and end‑user communication
Continuous improvement and ownership mindset

Education and Experience

Bachelor’s degree in Information Technology, Computer Science, Business Information Systems, or a related field is preferred; equivalent hands‑on experience will also be considered. Candidates should typically have several years of experience supporting Microsoft 365 administration, workflow automation, scripting, collaboration platforms, or related modern workplace technologies.

Success in This Role

Success in this role will be measured by the ability to deliver reliable Microsoft 365 solutions, improve business workflows, reduce manual administrative effort through automation, support effective collaboration platforms, and provide responsive, professional experiences for business users and stakeholders.

Benefits