Our Team

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.

Jared Rudolph, Esq.

Jared is a criminal defense attorney who has worked towards innovative solutions to intractable criminal justice problems in Baltimore, San Francisco, and Oakland. Jared volunteers as Executive Director of Prisoner Reentry Network, a 501(c)(3) that provides information and resources to individuals anticipating release from prison. He received his JD at George Washington University Law School.