Prentice first joined the city's development agency as a project coordinator in 1988 to help plan the Oregon Convention Center Urban Renewal Area. He left in 1993 to run his own land use planning and redevelopment business, and returned to the PDC in 1996 as a senior development manager. Most recently Prentice was in charge of the agency's efforts in the Downtown core.

Professionally, Prentice was a member of the American Institute of Certified Planners, the American Planning Association and the Urban Land Institute. Personally, he was an avid Harley enthusiast. Prentice served as an officer of the Rose City Harley Davidson Club and often took extended tours around the country with his wife and friends. He also was an active fundraiser and volunteer for numerous women's and children's causes.

Among his myriad accomplishments for the PDC, Prentice helped develop the Eastbank Park Master Plan and the last phases of the Rouse/Pioneer Place project. Most recently, he served as the Downtown Target Area Team leader directing the Commission's involvement in the Mid-Town Park Blocks, planning for the West End district, development of the Museum Place project and general Downtown retail vitality.