When I called them about this exact issue what they told me is to register the second contact with your name reversed (last name as the first name and first nam

When I called them about this exact issue what they told me is to register the second contact with your name reversed (last name as the first name and first name as the last name). Also use a different business email with the same domain for the second contact. That seemed to do the trick. One thing to take note of though is be very careful if you set up managed IDs and a verified domain through Apple Business Essentials. It locks devices down pretty heavily. I'm not familiar with this area of IT and didn't know that, although it might be pretty obvious to those who work in the space.