I managed to enroll some contacts (with a deal associated) on a specific places in the workflow by:
1. Creating an IF branch. Here I set as conditions to be met something like Deal creation date before…
2. Creating a step that points to the workflow where I wanted to enroll the contact.
3. Enroll them manually (not many deals in my case).
4. Delete the branch to put everything back where they belogn.
Just as a best practice, I realized that a workflow that is being iterated or created for the best time should always have a delay for X days as a last step to avoid this problem.