How to Sync Redtail and Calendly using Retriever for Tailwag and the Calendly-Outlook Plug-in

Calendly works with your calendar to automatically check availability and help you connect with your best contacts, prospects, and clients. We do not have a direct integration with Calendly, but through the use of Retriever for Tailwag and an Outlook Plug-in that Calendly provides, we can connect our platforms!


Please note: If you are able to use Retriever Cloud*, please follow one of the two articles below to connect Redtail and Calendly via our Retriever Cloud program.

Retriever Cloud for Office 365 – Calendly Sync

Retriever Cloud for Google – Calendly Sync


  • Under the Calendar Connection menu in Calendly, select Outlook Plug-in:


  • You will then be prompted to download the Plug-in:


  • On the Calendly webpage, after choosing to download, you will be given a unique key:


  • Enter the unique key into the Calendly application that appears on your desktop.
  • This is also where you will select the Outlook calendar Calendly will connect to.
  • This should be the same calendar that Retriever for Tailwag is connected to.


  • Choosing Advanced in the Settings window will allow you to manage additional Calendly settings:


  • After saving your settings, the setup is complete! You will then see the Calendly Plug-in home screen.
  • On this screen, you can access the same settings window as we saw in the setup.
  • There is also an option to Sync Now to force a sync between Calendly and the chosen Outlook Calendar.


  • Please Note: This Outlook plug-in will not appear in the normal Outlook add-ins. You will need to search your PC for “Calendly Plugin for Outlook” in order to access the application:


  • After the setup is complete, you may test this by adding a test event within Calendly:


  • Remember you have an option within the Calendly Outlook Plug-in app to Sync Now if you do not see the item appear in the Outlook Calendar immediately.


  • You should then see your new Calendly items in Outlook.
  • The next time Retriever for Tailwag syncs with this same Outlook calendar, the items will then sync to the Redtail CRM.
  1. mceclip9.png
  2. mceclip10.png


For assistance in enabling Retriever for Tailwag, please Click Here.

For further help within Calendly, please Click Here.

Was this article helpful?
0 out of 0 found this helpful
Have more questions? Submit a request


Powered by Zendesk