Microsoft 365 · Chicago Metro

Microsoft 365 Management and Support for Chicago Businesses

Buying Microsoft 365 takes five minutes. Running it well is a different job: the right licenses for the right people, security that is switched on rather than left at the defaults, Teams and SharePoint organized so people can find things, and someone who handles the joiners, leavers and “I can’t get into Outlook” moments.

Datastrive manages Microsoft 365 for Chicago businesses as part of our managed IT services or as a standalone service. We set it up properly, keep it secure, review what you’re paying for and support your team when something doesn’t work.

If you’re paying for licenses you don’t use, we’ll tell you. We treat your money like it’s ours.

  • Based in Chicago, serving businesses across Cook, DuPage, Lake and Will counties
  • Licensing reviewed against what your people actually use
  • Security configuration built around the CIS Controls framework
  • Part of our cloud services or managed as a standalone service

Schedule a Microsoft 365 Review

Tell us a little about your business and someone from our team will reach out to set up a time. Your information stays private.

Microsoft 365 Chicago

Most Microsoft 365 Problems Aren’t Microsoft’s Fault

Employee working in Microsoft 365 on a laptop and smartphone

Microsoft 365 is built to be easy to adopt, which means a lot of it ships at settings that suit adoption, not security. Licenses get added one at a time as people join and rarely get removed when they leave. Shared folders sprawl. Teams multiply.

None of that is a product problem. It’s a management problem, and it’s the work we take off your plate.

Good Microsoft 365 management is mostly invisible: people sign in, find their files, and nobody has a shared password on a sticky note.

Common Problems

Where Microsoft 365 Usually Goes Wrong

These are the issues we find most often when we first review a Chicago business’s Microsoft 365 tenant.

Paying for the Wrong Licenses

Business Basic, Standard, Premium, E3, E5: the differences matter, and most businesses end up with a mix chosen at different times by different people. Some users have more than they need, others are missing features they should have.

Security Left at the Defaults

Multi-factor authentication, conditional access, admin roles, external sharing and mailbox forwarding rules all need deliberate configuration. Defaults are a starting point, not a security standard.

Files Nobody Can Find

SharePoint sites and Teams created without a plan turn into another version of the messy shared drive. Structure and permissions decide whether people actually use them.

Leavers Who Still Have Access

When someone leaves, their account, mailbox, shared files and devices need handling the same day. Without a process, former employees keep access far longer than anyone realizes.

Nobody Owns the Tenant

Admin rights end up with a former employee, a previous provider or a personal email address. Knowing who controls your Microsoft 365 tenant, and documenting it, is the first thing we check.

Scope

What Our Microsoft 365 Services Cover

Licensing and Plan Review

We review who has which license, what they actually use and where a different plan would fit better. Licensing is handled as part of our IT vendor management.

User Administration

New starters set up with the right access, leavers removed properly, and mailboxes, shared mailboxes, groups and distribution lists kept tidy.

Teams, SharePoint and OneDrive

Sites, Teams and permissions organized around how your business works, so files have one home and people can find them.

Security Built Around a Recognized Framework

Multi-factor authentication, conditional access, admin roles, sharing policies and alerting, set up and reviewed around the CIS Controls v8.1 framework. For continuous threat monitoring, see Microsoft 365 security and MDR.

Migration

Moving from on-premises Exchange, Google Workspace, another tenant or a file server. See Microsoft 365 migration for how we plan and run it.

Microsoft 365 Backup

Microsoft keeps your data available, but its retention isn’t the same as a backup you control. Separate Microsoft 365 backup is part of our backup and disaster recovery service.

In Practice

How Microsoft 365 Management Works With Datastrive

We start with a review, fix the foundations you agree to, then keep the tenant in good shape month to month.

ReviewWe look at your tenant, licenses, security settings and how your team uses Teams, SharePoint and OneDrive.
Fix the foundationsAgreed priorities first: security gaps, licensing changes and the structure problems causing daily friction.
Ongoing managementUser changes, support requests, security reviews and license checks handled as part of your agreement.
DocumentationAdmin access, settings and decisions written down in a format your team can read, so nothing depends on one person’s memory.

No configuration makes an account impossible to compromise, and we won’t claim otherwise. What we commit to is a documented setup, reviewed regularly, with someone accountable for it.

Comparison

Microsoft 365 or Google Workspace?

Microsoft 365
Google Workspace
Often suits
Teams using Office desktop apps and Windows devices
Teams that work mainly in the browser
Files
SharePoint, OneDrive and Teams
Google Drive and shared drives
Device management
Included in Business Premium (Intune)
Available on higher Workspace plans
Datastrive support
Managed and supported
Managed and supported

Most of the Chicago businesses we work with run Microsoft 365, but some are better suited to Google Workspace, and we support that too. See Google Workspace management, or read about cloud migration if you’re planning a move.

Industries

Microsoft 365 Across Chicago Industries

Law firms need careful sharing controls around client documents. Healthcare practices need access set up around patient information. Financial services firms need retention and mailbox controls that stand up to review. Non-profits can often access discounted licensing.

We set Microsoft 365 up around the way your sector works.

See our industries page for the full list, including legal, healthcare, financial services, manufacturing and nonprofits.

Law firmsHealthcare practicesManufacturersFinancial services firmsProfessional services firms
Service Area

Microsoft 365 Support Across Chicago and the Suburbs

Most Microsoft 365 work is handled remotely, with onsite visits when a device, an office setup or a migration needs someone in the room. We work with businesses throughout Chicago and the surrounding area, including Skokie, Schaumburg, Naperville, Oak Brook, Elk Grove Village, Rosemont, Downers Grove and Aurora. Full coverage details are on our Chicagoland service area page.

Our office6351 W Montrose Ave, Chicago, IL
Counties we coverCook, DuPage, Lake and Will
Getting Started

Getting Started With Datastrive

1

A conversation about how you use Microsoft 365.

You tell us what’s working, what’s frustrating and who manages it today.

2

A review of your tenant.

We look at licenses, security settings, admin access and file structure, and tell you what needs fixing and what doesn’t.

3

A plain-numbers proposal.

You get a written plan covering what we would manage and what it costs. No obligation and no pitch for licenses you don’t need.

FAQ

Frequently Asked Questions About Microsoft 365 Management in Chicago

Which Microsoft 365 plan is right for our business?
It depends on your user count, security needs and the features your team actually uses. For many small and mid-sized businesses, Business Premium is a good fit because it includes device management and stronger security tools. We recommend a plan after reviewing how you work, and we’ll say so if a cheaper plan does the job.
Can you manage Microsoft 365 without a full managed IT agreement?
Yes. Some businesses come to us for Microsoft 365 management only. Scope and pricing depend on your user count and what you need covered.
Isn’t Microsoft 365 already backed up by Microsoft?
Microsoft keeps the service running and holds deleted items for a limited time, but that isn’t the same as an independent backup with point-in-time restore. We recommend separate Microsoft 365 backup for most businesses.
Can you clean up our Teams and SharePoint?
Yes. We review what exists, agree a structure with you, consolidate where it makes sense and fix permissions so files have a clear home.
How do you handle employees leaving?
With a documented offboarding process: account blocked, mailbox converted or delegated, files transferred, devices recovered and access to shared resources removed, on the day you tell us.
Do you help with Microsoft 365 security?
Yes. Security configuration is part of how we manage Microsoft 365, built around the CIS Controls framework. For continuous monitoring and response, see our Microsoft 365 security and MDR service.
How do existing clients request Microsoft 365 support?
Through the client portal at portal.datastrive.com, by email at [email protected], or by phone at (773) 863-3868.
Microsoft 365 Review

Get More Out of the Microsoft 365 You’re Already Paying For

Tell us what’s frustrating your team about Microsoft 365 today. We’ll review your setup, tell you what needs fixing and what doesn’t, and explain what ongoing management would look like.

Schedule a Microsoft 365 Review

Tell us a little about your business and someone from our team will reach out to set up a time. Your information stays private.