Okamoto was born and raised in Seattle, earning his bachelor's degree in psychology and his master's in public administration from the University of Washington.

[4] The report stated there "was a lack of adequate oversight by senior members of the Port’s executive staff," which included Okamoto.

[4] In April 2015, City Councilmember Sally J. Clark announced that she would resign her seat to take a job at the University of Washington.

[7] He was one of eight finalist, which included former councilmember Jan Drago and activist Sharon Maeda, that the full council to vote on by simple majority.

[8] Councilmember Kshama Sawant vehemently argued against Okamoto, citing The Stranger (newspaper) articles about the audits during his time at the Port of Seattle.