Ruben grew up in Cambridge, Massachusetts, and went through its public schools. He was a bright kid who struggled inside a system that wasn't built around him, and he watched classmates' futures get sorted by things none of them controlled. He went into teaching because of it.

That choice took him to Teach For America in Memphis, to five years as a teacher and Grade-Level Lead at KIPP Bayview Academy in San Francisco, and to a role as Assistant Principal of Humanities at Caliber Beta Academy in Richmond, California. In each of those jobs he was working on the same problem: how to build schools where students set their own goals and develop the will and the skill to reach them. When he felt he hit the limits of what one classroom or one building could change, he earned an Ed.M. in Education Policy and Analysis at the Harvard Graduate School of Education. He has since advised the Poughkeepsie Children's Cabinet and visited innovative schools across the country.

TVS was one of those schools. The families and educators there had already made the choice he'd been working toward: to build school around who learners are, and to treat their agency as the purpose of school instead of a reward for doing well in it.

Ruben partners with Head of Learning Design, Dr. Elizabeth Dean, on the learner experience and the launch of the high school. He also teaches 7th grade history at UP Academy Charter School of Dorchester.