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Remote M365 Administrator Jobs in Chicago, IL (NOW HIRING)

ENow Software

Product Owner (Remote)

Chicago, IL · Remote

$140K - $150K/yr

Understanding of enterprise IT environments and admin workflows * Experience in a small company or ... Opportunity to help shape the future of M365 monitoring and governance * Close collaboration with ...

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Remote M365 Administrator information

What are the key skills and qualifications needed to thrive as a Remote M365 Administrator, and why are they important?

To thrive as a Remote M365 Administrator, you need expertise in Microsoft 365 (M365) administration, troubleshooting, and security management, typically supported by relevant certifications like Microsoft Certified: Modern Desktop Administrator Associate or Microsoft 365 Certified: Enterprise Administrator Expert. Familiarity with tools such as PowerShell, Azure Active Directory, Exchange Online, SharePoint, and Teams is essential for effective system management. Strong problem-solving skills, effective communication, and the ability to work autonomously are standout soft skills for this remote position. These skills and qualifications ensure secure, efficient, and uninterrupted collaboration for organizations leveraging Microsoft 365 solutions.

What are some common challenges faced by Remote M365 Administrators, and how can they be overcome?

Remote M365 Administrators often encounter challenges such as managing user access and permissions across distributed teams, ensuring data security, and troubleshooting issues without physical access to user devices. Effective communication with end-users and other IT team members is essential to resolve problems efficiently. Utilizing remote management tools, staying up-to-date with Microsoft 365 updates, and establishing clear documentation practices can help overcome these challenges and maintain smooth operations.

What are Remote M365 Administrators?

Remote M365 Administrators are IT professionals responsible for managing and supporting Microsoft 365 (M365) services such as Exchange Online, SharePoint, Teams, and OneDrive, but they perform their duties remotely. They handle user account management, security and compliance settings, troubleshooting, and system updates without being physically present in an office. These administrators ensure that organizations can securely collaborate and communicate using the M365 suite, often utilizing cloud-based tools and remote access solutions. Their role is crucial for businesses with distributed teams or those adopting hybrid or fully remote work environments.

What is the difference between Remote M365 Administrator vs Remote Microsoft 365 Support Specialist?

AspectRemote M365 AdministratorRemote Microsoft 365 Support Specialist
CertificationsMicrosoft 365 Certified: Enterprise Administrator Expert, Microsoft 365 Certified: Modern Desktop Administrator AssociateMicrosoft 365 Certified: Fundamentals, Microsoft 365 Certified: Security Administrator Associate
Work EnvironmentManage and configure Microsoft 365 services, perform administrative tasks, handle user managementProvide technical support, troubleshoot user issues, assist with service outages
Employer & Industry UsageIT departments in various industries, cloud service providersHelp desks, IT support teams, customer service in organizations using Microsoft 365

The Remote M365 Administrator focuses on managing and configuring Microsoft 365 services, requiring advanced admin certifications. In contrast, the Remote Microsoft 365 Support Specialist primarily provides user support and troubleshooting. Both roles are essential in organizations utilizing Microsoft 365 but differ in responsibilities and skill levels.

What are the most commonly searched types of M365 Administrator jobs in Chicago, IL? The most popular types of M365 Administrator jobs in Chicago, IL are:
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What cities near Chicago, IL are hiring for Remote M365 Administrator jobs? Cities near Chicago, IL with the most Remote M365 Administrator job openings:
Remote M365 Administrator jobs near you
Infographic showing various Remote M365 Administrator job openings in Chicago, IL as of May 2026, with employment types broken down into 100% Full Time. Highlights an 80% In-person, and 20% Hybrid job distribution.
Product Owner (Remote)

Product Owner (Remote)

ENow Software

Chicago, IL • Remote

$140K - $150K/yr

Full-time

Posted yesterday

Job description

About the Role

This is a fully remote position. We are seeking an experienced Product Owner to help drive clarity, focus, and execution across our Microsoft 365 product portfolio, including monitoring, reporting, governance, and adoption solutions. This role sits at the intersection of customers, engineering, support, and leadership, translating real-world customer problems into clear, actionable product requirements.

This is a hands-on role for someone who enjoys working close to the product, customers, and engineering, and who thrives in an environment where ownership matters more than titles.

Key Responsibilities

Product Ownership & Execution

  • Own and maintain the product backlog across the ENow suite of products
  • Write clear, concise Epics, Features, and User Stories with strong acceptance criteria
  • Ensure backlog is prioritized, groomed, and ready to support a 60-day development horizon
  • Partner with Engineering to estimate, scope, and sequence work
  • Act as a decision-maker on scope and trade-offs during development

Customer & Market Alignment

  • Gather input from customers, support, sales, and implementation to identify pain points and opportunities
  • Translate customer challenges into practical, high-value solutions
  • Validate requirements through customer conversations, support data, and usage insights
  • Help balance enterprise customer needs with scalable product design

Collaboration & Communication

  • Serve as a bridge between Engineering, Support, Sales, and Leadership
  • Participate in sprint planning, backlog refinement, demos, and retrospectives
  • Clearly communicate what is being built, why, and when
  • Support pre-sales and demo readiness by ensuring consistent functionality and data
  • Periodically deliver product demos and technical walkthroughs to prospects and partners
  • Support Sales by explaining product capabilities, use cases, and value propositions

Product Quality & Outcomes

  • Define success criteria for features
  • Ensure features align with security, compliance, and least-privileged access principles
  • Review beta deployments to validate that delivered functionality meets expectations
  • Continuously refine features based on feedback and real-world usage
What Success Looks Like (First 6–12 Months)
  • Engineering consistently has a clear, prioritized backlog
  • Fewer requirement-driven reworks and mid-sprint changes
  • Improved alignment between customer needs and delivered features
  • More confident demos and sales conversations
  • Tangible improvements in customer outcomes (e.g. Better governance posture)
QualificationsRequired:
  • 5+ years of experience as a Product Owner, Business Analyst, or similar role
  • Experience working with Agile / Scrum teams
  • Strong ability to write clear requirements and acceptance criteria
  • Comfortable working closely with developers and technical stakeholders
  • Experience in SaaS or enterprise software environments
  • Excellent communication and prioritization skills
  • Familiarity with Microsoft 365, Entra ID (Azure AD), Exchange, Teams, SharePoint, or Power Platform
Preferred:
  • Experience with monitoring, security, governance, or analytics products
  • Understanding of enterprise IT environments and admin workflows
  • Experience in a small company or startup environment
  • Exposure to tools like Azure DevOps, Aha, Confluence, or similar

The salary range for this role is $140,000 - $150,000. ENow offers a competitive total rewards package which includes base salary and a comprehensive benefits & perks package. Exact compensation is determined based on a number of factors including experience, skill level, location, and qualifications which are assessed during the interview process. Additional details about total compensation and benefits will be provided by our Recruiting Team during the hiring process. In addition to the salary range listed, this role offers a meaningful, performance-based variable component. A significant portion of total compensation (up to 25%) is tied to measurable outcomes.

  • High-impact position with direct influence on product direction and customer outcomes
  • Opportunity to help shape the future of M365 monitoring and governance
  • Close collaboration with leadership and engineering
  • Flexible environment where ownership and initiative matter
  • A team that values clarity, accountability, and practical execution

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