Cheerful + Outlook integration

How the Outlook integration works

Campaign outreach, follow-ups and inbox sync run on Gmail or an SMTP/IMAP mailbox; Cheerful has no native Outlook sign-in for sending campaigns.

What can you do with Cheerful and Outlook?

4 ways influencer teams use this connection today. Each one is something the agent does now, not a roadmap item.

• Book influencer calls on my Outlook calendar

  When a creator asks to hop on a call, ask the agent to find a time that works on your Outlook calendar and create the event with the creator invited.

  1. Creator asks to talk
  2. Agent finds a free slot
  3. Outlook event, creator invited

• Search Outlook for past conversations with a creator

  Search your Outlook mailbox for past conversations with a creator or agency before re-pitching, so you do not open with a pitch they already declined.

• Send a one-off email from my Microsoft 365 address

  For a contract or invoice that must come from your company Outlook address, the agent can draft it in Outlook for you to send or send it directly.

• Move or cancel a creator call in Outlook

  If a creator needs a different time, the agent can update or cancel the Outlook event instead of you editing it by hand.

What Cheerful's agent can do in Outlook

Outlook exposes 287 actions to Cheerful’s agent. The ones used alongside creator campaigns:

• Find meeting times across attendees
• Create, update or cancel calendar events
• Read your schedule and list events
• Search and list messages
• Create a draft or a draft reply
• Send an email or a reply

How to connect Outlook to Cheerful

Setup takes 3 steps. Connected apps are added from the app catalogue in Settings.

1. 1

   In Cheerful, open Settings, go to Integrations and search the catalogue for Outlook.

2. 2

   Sign in with your Microsoft account through Microsoft’s consent screen. Some organizations require an admin to approve the app first.

3. 3

   In the chat that opens, ask for what you need: a meeting, a search or a draft.

What the Outlook integration does not do

Stated plainly, so you can plan around it before you connect.

Cheerful and Outlook: common questions

Does Cheerful work with Outlook?

Partly. Outlook is a connected app, so Cheerful’s agent can use your Outlook calendar and mail for meetings, searches and one-off emails. Campaign sending and inbox sync need Gmail or an SMTP/IMAP mailbox.

Can I send influencer outreach from Outlook with Cheerful?

Not through the Outlook connection. A Microsoft 365 mailbox can be connected for campaigns with SMTP and IMAP credentials if your administrator allows that access.

Does Cheerful sync Outlook replies into its inbox?

No. Replies that arrive in Outlook are not synced into Cheerful’s inbox. For campaign replies, connect a Gmail mailbox, or a Microsoft 365 mailbox over SMTP and IMAP where your admin allows it.

Why can’t I connect Outlook to Cheerful?

Your Microsoft 365 admin may block third-party app consent. If sign-in fails, ask the admin to approve the app.

Is the Outlook integration free?

Connecting Outlook is available in Cheerful, which is free to start.

Often connected alongside Outlook

• GmailNative integration · EmailSend outreach and follow-ups from your own inbox, with reply drafts
• Google DriveConnected app · FilesA folder per campaign or creator, with briefs and files shared for you
• SlackNative integration · Team chatReply alerts and one-tap gift approvals in your team’s channel
• HubSpotConnected app · CRMLog opted-in creators as contacts and collaborations as deals

See all integrations, or read which tools Cheerful integrates with for the native integrations and the ones that do not exist yet.