Prior to attending law school, Jonathan led as a Captain and infantry officer in the U.S. Marine Corps. During his 10 years of service, Jonathan served in a variety of billets, including leading rifle platoons in combat during Operation Iraqi Freedom and commanding a 150-Marine rifle company performing security and training exercises in Southeast Asia, as well as conducting counter-piracy operations in Somalia, advising U.S. diplomatic posts in Bahrain and Pakistan on security protocols, and managing complex military projects and programs as a staff officer.

Jonathan is a member of the International Association of Privacy Professionals, and has received the CIPP/US and CIPP/E certification. He is also on the Executive Committee of The Honorable William A. Ingram Inn Chapter of the American Inn of Court.

Active in the community, Jonathan currently serves as the Board Chair of HomeFirst, a 501(c)(3) non-profit corporation and the largest service provider in Santa Clara County committed to ending homelessness with operational budget of $50 Million, and serves on the Wine Country Marines board, a 501(c)(3) nonprofit corporation that supports the transition of service members and their family members to civilian life and provides support for the recovery and assistance during times of crisis, injury, or death.