No. The same Account Holder can only have ONE email address on the Enrollsy Account.
There can be a second email address associated with the Secondary Account Holder. We have a Shared Access feature that allows a Primary Account Holder to add additional people who can independently sign in using their own email addresses.
However, if the Primary or Secondary Account Holder has another Account with the same email address, they will NOT be able to log in. They will need to change the email address on one of the accounts.