Can I send messages to different numbers for the same HubSpot Contact?

No. Sakari can only pair one telephone number with each Contact record synced from HubSpot.  Once a Contact record and telephone number are paired in Sakari, that number is used exclusively for sending messages to that Contact.
 
This helps both you and Sakari align with industry best practice for SMS opt-in, as typically end-users only possess/provide one telephone number to which they agree SMS can be sent.

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