Hi Mitch,
I'm not aware of a way to do that with Outlook.
The first solution that comes to mind is building a small web based tool that lets you upload the current attachment for a profile, have their details in there, and an enabled/disabled flag too so you can stop for people that leave, and a convenient "send all" button that sends the current attachment to all enabled profiles when you click it.
Is there a dept at your company that can build that for you? They may have some additional ideas. Don't forget to be careful with any sensitive / personal information being stored.