Microsoft 365, SharePoint and Business Applications

RJ2 Technologies is a managed IT provider in Deer Park, Illinois, and has been migrating Chicago-area businesses onto Microsoft 365 and SharePoint since well before either had its current name. We handle the whole move: tenant setup and licensing, mailbox migration from on-premises Exchange, Google Workspace or a hosted POP account, file shares lifted off an aging server into SharePoint and OneDrive, and the security baseline (multi-factor, conditional access, blocked legacy authentication) that should be turned on the same week and usually is not. We also support the line-of-business applications that sit alongside all of that, the ERP, the practice management system, the accounting package your business actually runs on. Jeff Dann founded the company in 1998 and it has been in the northwest suburbs the whole time.

Can RJ2 Technologies be our Office 365 migration partner in Chicago?

Yes. RJ2 Technologies plans and runs Microsoft 365 and Office 365 migrations for businesses across Chicago and the Chicago suburbs, from a ten-person office moving off a hosted mail account to a company retiring an on-premises Exchange server.

Shawn Meyer, Director of Professional Services, owns this work. He has over 30 years in the industry, 21 of them at RJ2, and he takes the engagements where a client’s infrastructure gets rebuilt rather than patched. A migration is one of those. It is the moment where the decisions somebody made in 2011 either get carried forward for another decade or get fixed.

What a migration engagement covers, in the order it happens:

1. Discovery. Mailbox count and sizes, where mail lives now, how big the file shares are, and the full list of things that send email without a person involved: the copier that scans to email, the ERP that mails invoices, the alarm system, the backup software. This list is where migrations go wrong, and it is why discovery is not a formality.
2. Licensing. Which Microsoft 365 plan each user actually needs. Not everyone needs the same one, and the difference between Business Standard and Business Premium is the security stack, which matters more than the app list.
3. Tenant setup and domain verification. Provision the tenant, then prove you own the domain by publishing a TXT record at your DNS registrar.
4. Identity. Decide between cloud-only accounts and syncing from an existing on-premises Active Directory with Entra Connect. If there is a domain controller in a closet, this decision has to be made deliberately, because reversing it later is unpleasant.
5. Pre-stage the mail. Copy mailboxes across before cutover so the final sync moves hours of mail rather than years of it. The method depends on the source: cutover migration for a small Exchange environment, staged or hybrid for a larger one, a third-party tool for Google Workspace or IMAP.
6. Cutover. Change the MX record so new mail lands in the new tenant, update autodiscover, and set SPF, DKIM and DMARC so your mail keeps arriving in other people’s inboxes instead of their junk folders. This is usually scheduled for a Friday evening.
7. Delta sync. Sweep anything that arrived at the old system during the cutover window.
8. Workstations and phones. Outlook profiles rebuilt, mobile devices reconfigured, that copier pointed at a new SMTP relay. This is the part clients underestimate and the part that determines whether Monday morning is calm.
9. Security baseline. Multi-factor authentication, conditional access, legacy authentication blocked, admin roles cleaned up. Turning MFA on is also what breaks the last few old applications still using basic authentication, which is why it belongs inside the migration window and not three months later.
10. The week after. Someone answers the phone while people find the things they cannot find.

How do you set up SharePoint for a small business?

SharePoint setup for a small business starts with deciding what belongs in SharePoint versus OneDrive versus Teams, because putting everything in the wrong one is the mistake that takes two years to surface and a weekend to unwind. As a rule: OneDrive is one person’s working files, a SharePoint document library is the shared record the company keeps, and Teams is a conversation layer that stores its files in SharePoint anyway.

How RJ2 builds it:

• A flat set of sites, not a deep folder tree. One site per team or function (Finance, Operations, Sales) rather than one giant site with folders eleven levels down. People migrating off a file server want to recreate the F: drive exactly. That is the instinct to resist.
• Permissions through Microsoft 365 groups, not per-file sharing. Access follows the group, so when someone changes roles you change one membership instead of hunting through libraries. A site where half the folders have custom permissions is a site nobody can audit.
• Metadata and views where they earn their keep, and plain folders where they do not. Not every library needs a taxonomy.
• Versioning and retention turned on deliberately, so an overwritten file is a two-minute fix.
• External sharing set at the tenant level first, then relaxed per site if the business needs it. The default should be a decision, not an accident.
• OneDrive sync and Known Folder Move so Desktop, Documents and Pictures back up without anyone being asked to change how they work.
• The migration itself. File shares move with the SharePoint Migration Tool, and the two things that reliably break are file paths longer than SharePoint allows and filenames with characters Windows tolerated and SharePoint does not. Both get found and fixed before the move, not during.

What does a Microsoft 365 setup for a Chicago small business include?

A Microsoft 365 setup is more than buying licenses and handing out passwords. RJ2 provisions the tenant, moves the mail and files, configures the identity and security settings that ship turned off, and gets every workstation and phone reconnected before anybody has to work on a Monday.

For a small business specifically, the parts that matter most and get skipped most often:

• Multi-factor authentication on every account including the admin accounts, especially the admin accounts
• Legacy authentication blocked, because MFA on an account that still allows basic auth is not on
• A named break-glass admin account that is documented and stored somewhere findable
• SPF, DKIM and DMARC published, so your invoices reach customers
• Backup for Exchange Online, SharePoint, OneDrive and Teams, which Microsoft does not provide in the way most people assume (this is covered on our backup and disaster recovery page)
• Shared mailboxes and distribution lists rebuilt properly instead of carried over as somebody’s personal mailbox with the password written down

What about the applications that are not Microsoft?

Most companies run at least one application that the whole business depends on and Microsoft did not write: an ERP, a practice management system, a dental or legal or manufacturing package, an accounting platform. RJ2 supports those alongside the Microsoft stack, which in practice means owning the parts the software vendor will not.

That is usually the server or cloud instance it runs on, the database, the backups, the integration with email, the workstation side, and being the one who calls the vendor when it breaks so your staff does not spend an afternoon on hold. We also sit in on selection when a company is choosing between systems, because the question of what it costs to run is one the sales demo never covers.

Do you set up Microsoft 365 for businesses in Chicago and the Chicago suburbs?

Yes. RJ2 Technologies works with small and mid-sized businesses in Chicago and throughout the Chicago suburbs, from our headquarters at 21660 W. Field Parkway, Deer Park, IL 60010.

Being in the northwest suburbs matters more on a migration than on most work, because cutover weekends and workstation days are the times somebody needs to be in your building. The space at 333 S. Wabash Ave., Suite 2700 is a working space our engineers use when they are downtown for a client, not a staffed office.

Related: Line of Business Applications | Managed IT Services | Cybersecurity Services | Frequently Asked Questions

Further reading: Cloud Migration Services in Chicago: What the Move Actually Involves

Frequently asked questions

Who is a good Office 365 migration partner in Chicago?

Look for a provider who asks about your copier and your ERP before they quote the job, because the systems that send email without a person involved are what break during a cutover. Ask which migration method they plan to use and why, and ask what happens on the Monday after. RJ2 Technologies has run Microsoft 365 migrations for Chicago-area businesses out of the northwest suburbs since 1998, and Shawn Meyer, our Director of Professional Services, owns these engagements personally.

How do you set up SharePoint for a small business?

Start by separating what belongs in OneDrive (one person’s working files) from what belongs in a SharePoint document library (the company’s shared record). Then build a flat set of sites by team rather than recreating the old F: drive folder tree, and grant access through Microsoft 365 groups instead of sharing individual files. Turn on versioning, decide external sharing deliberately, and migrate the old file share with a tool that reports which paths and filenames will not survive the move before you make it.

How much does a Microsoft 365 setup cost for a Chicago small business?

The license cost is per user per month and depends on which Microsoft plan each person needs, which is not the same plan for everyone. The setup and migration cost depends on how many mailboxes are moving, how much data is on the file server, and how many workstations someone has to touch. RJ2 scopes it after a discovery call rather than quoting a number that changes once we see the environment.

How long does an Office 365 migration take?

For a small business the calendar time is usually driven by data volume and workstation count rather than by the mail cutover itself, which typically happens over a single evening or weekend. Mailboxes are pre-staged in advance so the final sync is short, and file share migration to SharePoint runs in the background beforehand. The realistic answer for any specific company comes out of discovery.

Will we lose email during the migration?

No. Mail is copied to the new tenant before cutover, and after the MX record changes, anything that arrived at the old system during the switch is swept over in a delta sync. The visible disruption is usually that Outlook needs a new profile and phones need to be reconnected, which is scheduled and staffed rather than left to each person to figure out.

What is the difference between OneDrive, SharePoint and Teams?

OneDrive is your own working storage, SharePoint is where the company’s shared documents live, and Teams is a chat and meeting layer that stores its files in SharePoint underneath. Files shared in a Teams channel are actually sitting in a SharePoint library, which is why the two have to be planned together. Getting this split right at setup is much easier than untangling it two years later.

Can you migrate us from Google Workspace to Microsoft 365?

Yes, and it is a different job from an Exchange migration because mail, calendars, contacts and Google Drive each move by their own path. Shared drives and Google-native file formats need decisions made about them before anything moves rather than during.

Do you work with small businesses in the Chicago suburbs?

Yes. RJ2 Technologies is headquartered in Deer Park and works with small and mid-sized businesses across Chicago and the Chicago suburbs. Call 847-303-1194, or email sales@rj2t.com to set up a discovery call.