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Hey Matt,
Chili Piper has this feature. You can create a meeting type that includes multiple people, you could even use suggested times to include options for someone to book with multiple people right in the body of the email.
When you open the suggested times widget, there is a space in the bottom right of your screen to add additional emails. You can then select options only from that joint availability.
When the meeting is booked, it will be booked across all the calendars you selected. Here is some documentation that outlines a few different ways you can accomplish this. Feel free to reach out to me, Dan Cmejla, directly as well.
https://help.chilipiper.com/hc/en-us/articles/360058301213
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