Alex Gentilli is the Director of Investment Operations at the Colby College Office of Investment Management. He came to Colby after spending time in trading and investment operations at places like Arrowstreet Capital and The Baupost Group before moving to the allocator seat.

We get into building an operating model from a blank slate — digitizing the investment book of record, selecting a portfolio management system, standing up a research management system, and putting cash controls and capital call discipline that had been part of the college treasurer’s office for years.

Alex describes the common tech stack build as a New England farmhouse — rooms added one at a time as the need came up — stepping back and decided it was time to redesign the house than do another addition.

We also dig into how he actually runs vendor selection: a weighted rubric, scoring each product immediately after the debrief to beat common organizational challenges and best ways to run a process.