Jacob Sills - CEO

After working in private equity and investment banking, Jacob’s passion for criminal justice reform led him to start Uptrust. Jacob believes that innovation, efficiency and kindness will solve our greatest criminal justice issues. Jacob received his B.A. from Cornell University and his M.B.A. from the Wharton School at the University of Pennsylvania.


Elijah Gwynn - CTO

Prior to joining Uptrust, Elijah was a full-stack software engineer at the Match Group (OkCupid) and applications developer at the NYC Department of Public Health. Elijah has 10+ years of experience building web applications using C, C++, Python, PHP and JavaScript. Elijah studied Computer Science at Carnegie Mellon University.

Seann Riley - Director of Partnerships

Riley brings to Uptrust nearly two decades working as a public defender. As Deputy Director of The Bronx Defenders, Riley created the first of its kind, interdisciplinary training for new attorneys providing the skill set necessary to address the enmeshed penalties stemming from criminal justice and family court involvement. Harvard Law School recognized his public interest efforts and awarded him with the Wasserstein Fellowship. Riley’s experience also includes serving as the Project Director for The Center for Holistic Defense where he provided technical assistance to approximately 50 public defender offices across the country. Prior to The Bronx Defenders Seann was the recipient of the E. Barrett Prettyman Fellowship at the Georgetown Law Center where he was a Supervising Attorney in the Criminal Justice Clinic. A graduate of Tulane Law School (JD) and Georgetown Law Center (Master of Laws), Riley holds a Masters of Social Work from the University of Michigan and a Bachelor of Arts degree in government from Georgetown University. He is  an adjunct professor at CUNY Law School, and was previously a Supervising Attorney in the Adolescent Representation Clinic and Holistic Defense Externship Clinic at Columbia Law School, and an adjunct professor at Fordham Law School.

William Servos - Lead Backend Engineer

Will leads all of Uptrust's customer integrations and support. Prior to joining Uptrust, Will had backend and support software engineering roles with Schaefer Systems International, Sedgwick CMS, and Argent Software. His personal experiences with the justice system and time teaching in marginalized communities at Our Piece of the Pie and Organized Parents Make a Difference drive his passion for Uptrust's work. William received his B.S. in Computer Science from Trinity College.