Simon is the COO of BillingNav, they help health plan members with balance billing. Prior to that, he founded and was CEO of JoinMagnify.com in San Francisco. The company was acquired by Citizn Company.

The degree program he undertook during his time at Maynooth cemented his interest in conflict/dispute resolution. It also expanded the range of possibilities for his career in this area - from international, to commercial, and family conflicts. More specifically, he discovered his passion for online dispute resolution while in Ireland.

A 2015 Mitchell Scholar, Simon received is MA in Mediation and Conflict Intervention from the National University of Ireland, Maynooth (NUIM). During his year in Ireland Simon also served as a Guest Lecturer in the School of Business at Maynooth, as well as a Project Manager at Edward M. Kennedy Institute for Conflict Intervention.

Simon obtained his undergraduate degree from Cornell University.