For campaigns that target Known Personalities, the answer is yes. You can choose Group or Entity when creating a Cajole, and input the Group's name as PERSON ONE/PERSON TWO.
You are able to do this because we handle offers to Known Personalities offline, and are able to organize such campaigns in that environment.
For campaigns that target Everyday People, the answer is no. We don't have the feature built into our site that would allow us to automate delivery of a campaign to more than one targeted person, group or entity for now.
We are working to build that into our system, and hope to allow this in the near future.