He is co-founder and CEO of OpenGov, a company that sells cloud software to local governments and state agencies.
[2] Bookman served as a law clerk to the Honorable Sandra S. Ikuta on the U.S. Court of Appeals for the Ninth Circuit, later working as a trial litigator at Keker, Van Nest & Peters in San Francisco.
Bookman helped lead a Rule of Law team on the task force that worked with the Afghan Department of Justice on corruption cases, such as the bribery scandal at the Dawood National Military Hospital.
[7] In September 2019, Bookman joined an expedition with mountain guide Garrett Madison to attempt a late season ascent of Mount Everest.
[9] In March 2020, Bookman filed a lawsuit seeking damages over the non-refundable expedition fee,[8] alleging the guide had canceled the trip for reasons unrelated to safety.