You just had a den meeting where you worked with five boys to complete four of the requirements for the Citizenship Pin. You could enter the exact same information into TroopTrack five times, or you could use the "Record Progress Bulk" workflow to do it all at once.
The "Record Progress" workflow is available from the Achieve badge drop down menu as shown below:
After you select an award, the requirements for the reward will appear. Check off the requirements you completed in the activity, like this:
Scroll to the bottom and press record progress.
That's it! Easy as pie.