Ryan was promoted to Sergeant in 2006, and as part of his duties supervised a Patrol Division squad and managed the department’s Field Training Program. Ryan was promoted to Captain in January of 2008 and was assigned to the Administrative Services Division, where his responsibilities included managing the department's 911 center and records office, conducting internal investigations, coordinating the field training program, and managing the budget. In late 2009, Ryan was transferred to the Criminal Investigative Division, where he managed the department's crime prevention programs and supervised the school resource officers and detectives.

        In 2011, Ryan was transferred to the newly created Professional Standards division, where his responsibilities included training, grant writing and research, monthly and annual statistical reports, and  internal investigations.  During that same time, Ryan created and coordinated the WPD's first ever Citizens' and Teen Police Academies.  In June of 2019, Ryan was transferred to the Support Services Division, where he managed the 911 Center, the Records Office, and facility maintenance.
        In April 2021, Ryan was promoted to Assistant Chief where he currently supervises the Administrative, Criminal Investigative, and Patrol Divisions along with managing the Records Office.  In the fall of 2022, Ryan received a Master Certificate upon graduation from the Professional Development Academy's High Performance Leadership program.
        Ryan and his wife Sherri enjoy the friendly atmosphere and lifestyle that Watertown provides, and find that it is a great place to raise their four children.