Cloud Migration Services in Chicago, Planned Around the Way Your Business Works
Moving to the cloud is rarely the hard part. The hard part is moving without losing a week of productivity, breaking the one application nobody documented, or finding out on Monday morning that half the shared drive didn’t come across.
Datastrive plans and runs cloud migrations for Chicago businesses moving file servers, email and business applications to Microsoft 365, SharePoint, OneDrive and hosted infrastructure. We start with what you have and what your team actually uses, then decide together what should move, what should stay and what should be retired.
And if something doesn’t need to move yet, we’ll tell you. We treat your money like it’s ours.
- Based in Chicago, serving businesses across Cook, DuPage, Lake and Will counties
- Discovery and a written migration plan before anything moves
- Cutover scheduled around your working day, with a rollback point
- Part of our cloud services or run as a standalone migration project
Schedule a Cloud Migration 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.
A Cloud Migration Is a Business Project, Not Just a Technical One
Most migrations that go badly don’t fail on the technology. They fail because nobody mapped which files belong to which team, which permissions matter, which old application still depends on a mapped drive, or what the accounting team needs on the first day of the month.
Our cloud services cover ongoing management once you are there. This page is about getting there: the planning, the move itself and the first weeks after.
The goal isn’t “in the cloud.” The goal is your team opening their files, email and applications the morning after the move and getting on with their work.
Where Cloud Migrations Usually Go Wrong
Most of the trouble in a migration is predictable. These are the problems we plan around before anything moves.
Nobody Knows What’s on the File Server
Years of shared folders, duplicate copies and permissions granted one person at a time. Moving all of it as-is just relocates the mess. Moving none of it leaves people searching for files in two places.
Applications With Hidden Dependencies
Line-of-business software, scanners, old macros and accounting tools often rely on a mapped drive, a local database or a license tied to a specific server. These need to be found before the move, not after.
Cutover Planned for the Wrong Moment
A weekend migration sounds safe until Monday arrives and the issues land on everyone at once. Timing has to fit month-end, payroll, busy seasons and who will be around to help.
Security Left at the Defaults
A new cloud environment is only as secure as its configuration. Multi-factor authentication, sharing settings, admin access and conditional access policies have to be set deliberately, built around the CIS Controls framework.
Nobody Owns the Weeks After the Move
A migration isn’t finished at cutover. Phones need reconnecting, a few files turn up missing, and someone has to answer the questions. Without a plan for the first weeks, the project quietly becomes your team’s problem.
What Our Cloud Migration Services Cover
Discovery and Assessment
We inventory servers, shared drives, mailboxes, applications and user permissions, and talk to the people who use them. The result is a clear picture of what exists and what each team depends on.
Migration Plan and Scope
A written plan covering what moves, in what order, what stays on-site, how permissions map across, the cutover window, the rollback point and who is responsible for each step.
File Server to SharePoint and OneDrive
Shared drives restructured into SharePoint sites and Teams that match how your business is organized, with personal files moved to OneDrive and permissions cleaned up on the way.
Security Built Around a Recognized Framework
Every migration is configured around the CIS Controls v8.1 framework from day one: multi-factor authentication, admin roles, sharing settings and alerting in place before users arrive. For the full security catalog, see our cybersecurity services.
Email and Mailbox Migration
Mailboxes, calendars and contacts moved from on-premises Exchange, Google Workspace or another Microsoft 365 tenant. For more detail on this part, see Microsoft 365 migration.
Applications, Servers and Post-Migration Support
Business applications assessed one by one: move to a cloud version, host elsewhere, or keep on a server for now. After cutover we support your team, clean up anything that didn’t behave as planned and document the new environment. Larger moves are run through our IT project management process.
How a Cloud Migration Works With Datastrive
Every migration follows the same order: understand what you have, agree the plan, prove it on a small group, then move everyone else.
We’ll be honest about what the migration involves, including any short windows where access is limited, rather than promising none at all.
Cloud Migration vs. Ongoing Cloud Management
Some businesses come to us for the migration only. Most keep us for the ongoing management because the team that planned the move already knows the environment. See Microsoft 365 management and backup and disaster recovery for what that ongoing work covers.
Cloud Migration Across Chicago Industries
Law firms need document access and confidentiality handled carefully. Healthcare practices have clinical applications that can’t simply be lifted into the cloud. Manufacturers often run production software that needs to stay close to the floor. Professional services firms want their people working from anywhere without remote-access headaches.
We plan the migration around how your sector actually works, not a generic checklist.
See our industries page for the full list, including legal, healthcare, financial services, manufacturing and nonprofits.
Cloud Migration Across Chicago and the Suburbs
Planning and most migration work happen remotely, with onsite visits for discovery and cutover support. 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 what you run today.
You tell us what’s on your servers, what your team uses and what you hope the cloud will fix.
A review of what should move.
We look at files, email and applications and tell you what makes sense to move, what doesn’t and why.
A written migration plan.
You get a scoped plan with sequence, timing, responsibilities and cost. No obligation and no pitch for work you don’t need.
Frequently Asked Questions About Cloud Migration in Chicago
What does a cloud migration usually include?
How long does a cloud migration take?
Will our team lose access during the migration?
Should everything move to the cloud?
Can you move us from a file server to SharePoint and OneDrive?
How is a cloud migration priced?
What happens after the migration is finished?
How do existing clients get support during the project?
Planning a Move to the Cloud? Start With What You Actually Have.
Tell us what you’re running today and what you’re hoping the cloud will fix. We’ll give you a straight answer about what should move, what shouldn’t, and what the project would involve.
Schedule a Cloud Migration 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.