Yes! With Shift4Shop, you can specify checkout questions that will only be asked to customers belonging to individual customer pricing groups.
Log into your Online Store Manager and, using the left navigation menu:
Go to Settings > General > Checkout Questions.
Click Add New at the top right side of the screen.
Specify the details of your question such needed.
Then, to ensure the question is only asked to a certain customer pricing group, you would use the "Customer Group" drop-down menu.
Click Add to complete the addition.
The question will then be asked as normal but only to customers who are logged in to their account and belong to the group you have specified.