Jacob joined Wikimedia as a lawyer in November 2014. Before arriving, he spent a year working for the United States Senate doing government investigations, where he worked on matters ranging from structured finance to Swiss data privacy to the ins and outs of high frequency algorithmic trading.

Before he started working, Jacob attended Harvard Law School where he studied several courses in intellectual property and taught copyright law through the edX program, and he did his undergraduate study at UC Berkeley, where he majored in History of Science with a minor in Japanese.

In his free time, Jacob is an avid gamer, including dice plus paper, cards, and video games.

The common thread that runs through what Jacob does is a love of trying to figure out complex systems, whether those are RPG stat systems, academic theory, or legal issues.