He began his law enforcement career with the Palo Alto Police Department in 1979, serving there for 12 years and promoting through the ranks to Lieutenant.In 1991, he left the Palo Alto Police Department to accept a position as a Police Captain with the Salinas Police Department, where he served for three years.
In 1994, he was appointed Chief of Police of the Redwood City Police Department, where he served for 12 years. During his tenure as Police Chief, Sheriff Bolanos focused on youth-oriented programs, and is credited with integrating a community oriented policing philosophy in the organization and bringing P.A.L. to the community.
In January 2007, Sheriff Bolanos was appointed as Undersheriff of San Mateo County by Sheriff Greg Munks. As the Undersheriff, he was responsible for the day to day operations of the Sheriff's Office which included oversight of the Crime Lab, Technology Services and Administration & Finance.