You do not need a 40-row feature matrix. You need mail that lands, calendars staff actually use, and a tenant you own — you@yourdomain.com, not a consumer inbox pretending to be a company.
Pick the suite your people will live in. Then do DNS and admin hygiene so deliverability is not a weekly ticket.
The job to be done
Most Orlando shops need the same core: branded email, shared calendar, file sharing that is not a USB stick, and a phone story that does not depend on one person’s Gmail.
Workspace / 365
Rented productivity suites at your domain. Orlando Web & IT helps with setup and migrations — we do not sell hosted mailbox products. See Microsoft 365 / Google Workspace.
When Google Workspace usually fits
- The team already lives in Gmail and Docs
- You want a light admin surface and strong sharing defaults
- Optional Google Voice should ride with the same account story
- You are leaving a consumer Gmail that has become “the company”
When Microsoft 365 usually fits
- Staff already live in Outlook and Excel desktop
- You need SharePoint / Teams as the shared filing cabinet
- Accountants, attorneys, or vendors expect .pst / Outlook workflows
- Windows PCs are the shop standard (see devices & peripherals)
What both need (the unexciting part)
Non-negotiables
- A domain you control, with clear admin ownership.
- SPF, DKIM, and DMARC published and monitored.
- 2FA on admin accounts. Shared passwords are how tenants get hijacked.
- A named person who can reset mailboxes when someone leaves.
- A migration plan if you are leaving another provider — not a Friday cutover hope.
Need a side-by-side for your actual tools? Contact Orlando Web & IT — we will tell you which suite matches the shop, not which logo is trending.