Hi ​@RyanBCN - Thanks for reaching out!

While this is not a change made on the Calendly side, I believe this is something that can be accomplished through Hubspot directly.
 

The default behavior of the Hubspot integration looks like this:

• Once an invitee books a meeting, the invitee will show as a contact in HubSpot.
  • If they are a new contact, they will show as a lead in the lifecycle stage.
  • The host will show as the contact owner.
  • We do not change the owner after the contact already has one; we leave the contact alone because we don't want to assume that the owner has changed.
• If the invitee was a pre-existing contact in HubSpot before the Calendly booking, then the contact will keep the original contact owner. The new Calendly booking will not change the contact owner.

Calendly does not directly adjust deals, but changing this can be achieved through using the Workflows feature in Hubspot. As an example, the workflow will look something like this:
 

This workflow essentially changes the Contact Owner to whoever the Host is on the Calendly’s side. You should be able to have this adjust the Deals within Hubspot as well.

I’d recommend reaching out to Hubspot’s support team to dig into this further, but I believe this is something you can adjust!