Sailsy and Outlook
Most AI sales tools treat Outlook as the afterthought — Gmail first, Microsoft “later”. Sailsy connects to both through the same rails, and everything on this site that says “your mailbox” means either one.
Connect Microsoft 365 and Sailsy reads the conversations and calendar you already have, builds contacts and companies from them, sorts leads by what actually happened, and drafts follow-ups that send from your own address.
Last updated 2026-09-25
| Feature | Sailsy | Outlook on its own |
|---|---|---|
| Read through Microsoft Graph, turned into contacts, companies and timelines | A mailbox — rules and folders, but no customer record | |
| Calendar | Meetings import into the activity timeline, including recurring series | Calendar and contacts live apart from any deal context |
| Feature parity with Gmail | Same connect flow, same extraction, same drafting and sending | n/a |
| Sign-in | Sign in with Microsoft and connect the mailbox through the same app registration | n/a |
| Staying connected | Tokens refresh on expiry rather than silently going stale mid-week | n/a |
| Turning it off | Disconnect in one click; the scan data has its own retention and purge | n/a |
Is Outlook support as complete as Gmail?
Yes. Mailbox reading, calendar import, drafting and sending all work the same way; they are separate adapters behind one shared flow. If a page on this site mentions Gmail, Outlook does the same thing.
Which Microsoft accounts work?
Microsoft 365 and Outlook.com accounts, through a standard Microsoft identity consent. Tenant admins control which third-party apps their users may grant access to, as with any Graph application.
Will Sailsy move my mail or change my folders?
No. Sailsy reads to build the CRM and writes only the messages you approve. Your folders, rules and retention policies are untouched.
Can I connect Outlook and Gmail at the same time?
You can connect both accounts, but one mailbox is active for sending at a time, and its calendar comes with it — calendar access is part of the mailbox grant rather than a separate connection. Connecting the second provider switches which one Sailsy sends from.
The verdict
If your company runs on Microsoft 365, the usual sales-AI answer is a Gmail-shaped product with an Outlook checkbox. This one treats them as equals, because half of B2B does not run on Google.
Outlook on its own is a mailbox and a calendar. Sailsy turns what is in them into a pipeline with a next move on every deal.