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.
Most Microsoft 365 Problems Aren’t Microsoft’s Fault

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.
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.
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.
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.
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.
Microsoft 365 or Google Workspace?
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.
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.
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.
Getting Started With Datastrive
A conversation about how you use Microsoft 365.
You tell us what’s working, what’s frustrating and who manages it today.
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.
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.
Frequently Asked Questions About Microsoft 365 Management in Chicago
Which Microsoft 365 plan is right for our business?
Can you manage Microsoft 365 without a full managed IT agreement?
Isn’t Microsoft 365 already backed up by Microsoft?
Can you clean up our Teams and SharePoint?
How do you handle employees leaving?
Do you help with Microsoft 365 security?
How do existing clients request Microsoft 365 support?
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.