[1] Day received his associate degree in Criminal Justice from Clackamas Community College in 1991, and received a bachelor's degree in Organizational Management from George Fox University in 2018.
Throughout his career, he has served as Captain of the Training Division and later as Commander of the Central Precinct, which covers Downtown.
[3][4] In 2018, Day was appointed Deputy Chief, a position he served in for a year before retiring in 2019.
[3][5] In January 2020, Day was appointed to the Board of Badge of Life and Public Safety Chaplaincy.
[2][4][8] As Chief, Day has been notable for an increase in "broken windows policing" and a crack down on property and vehicle theft.