Hello, @gershone
Yes, you can.
Regarding “if someone with a seat on our account is going to countersign the contracts is that a second envelope or the same envelope?” A: if such user is in the same line in the .CSV file so you don’t need a second envelope. In the .CSV file each line represents ONE envelope where you can have many columns as necessary, for example, columns for the external and/or internal recipients.
This video explains how to use Bulk Send:
This checklist explain everything you need in the .CSV file to be used for the Bulk send operation:
Bulk Send Checklist
https://dsucustomers.docusign.com/km-guide-docusign-bulk-send-best-practices-checklist/2135879
I hope that helps, if so, I’d appreciate your Like here.
Best,
Alexandre