To adjust the order the Schools display in, change the enrollment start date to be a day before the other school in order for it to appear first. For example, SIS Academy shows first with a Enrollment Date of 9/1/2015 before Brookfield School with an Enrollment Date of 9/2/2016. To have Brookfield School display before SIS Academy, navigate to:
  1. Core > Users > Edit User Profile Data
  2. Search for the User, and click into the Users record
  3. Scroll down to System Information
  4. Click Student Enrollment 
  5. Click Edit next to Brookfield School and edit the Date to be before SIS Academy which has a date of 9/1/2015, so enter 8/31/2015 on Brookfield

This will change the order the Schools display in on the Transcript so that Brookfield School displays before SIS Academy.