Santiago started his career in 1996 as a fifth grade teacher at Bruce-Guadalupe Community School, which is a part of the United Community Center on the near southside of Milwaukee. His entire educational career has been at the UCC and has served as a Teacher, Assistant Principal and now Middle School Principal of Bruce-Guadalupe and UCC Acosta Middle School. He earned his Bachelors and Masters from Marquette University and was a member of New Leaders for New Schools administrative training program. One of his favorite staff activities is hosting Book Clubs with members from his staff, to brainstorm new ideas and discuss how to better serve students.