When the TSTC Foundation announced it had awarded $1.4 million in scholarships in a single semester (up from $200k the year before) colleagues in financial aid assumed it was a typo. It also wasn't an overnight success: it was the result of a deliberate operational transformation - moving from manual spreadsheets and a limited portal to a centralized, full-cycle scholarship management system across eleven campuses. In this case study, TSTC Foundation staff walk through the full arc of that change, from the before state, the internal discussions, the implementation decisions, and the downstream effects they didn't anticipate (including how this impacted adjacent offices). This is an honest account of what transformation actually takes, not a polished success story, with concrete data points attendees can bring back to their own institutions.