Ms. Jessie Wyman plays a critical role in both Strategy 5’s business development initiatives, and in providing our clients with insightful analysis. She contributes directly to the firm’s work with innovative technologies, spatial design, data representation, and the firm’s commitment to creative problem solving. These skills are further manifested in our holistic approach to economic development, providing solutions to housing challenges, and imbuing the work with her design sensibilities associated with urban planning, environmental, and open space utilization.

Jessie has over a decade of experience in state and municipal planning, with a background in community and economic development, and urban design. She previously served as Director of Community Development for the Town of Reading, Massachusetts, where she led and implemented a range of economic and community development initiatives.

After receiving her master’s in urban design, Jessie worked with a Boston-based design firm on community-based planning and wayfinding projects, including the design of the Hull Artwalk Gateway. She also administered technical assistance for two projects funded through the Massachusetts Rapid Recovery Program (2021). Her professional skills extend to photography, 2D / 3D design, marketing, branding, website design, and more.

She assists in the management of the firm’s regular interaction with agencies and organizations such as the Massachusetts Municipal Association, MassHousing, the Massachusetts Housing Partnership, Consulting Planners of Massachusetts, American Planning Association, International Downtown Association, Urban Land Institute, and other import participants in our field.

Based in Massachusetts, Ms. Wyman is well placed to provide clients throughout New England with the personal service and attention to community history and culture that are a hallmark of Strategy 5’s work. She also plays an integral role in the firm’s work throughout the United States. Jessie holds a Bachelor’s degree in Community and Regional Planning from Iowa State University and a Master’s degree in Urban Design from Northeastern University.