The George Washington Region in Virginia comprises the City of Fredericksburg, and Counties of Caroline, King George, Spotsylvania, and Stafford. GWRideConnect, its Transportation Demand Management (TDM) agency, enables commuters to explore vanpool, carpool, and bus alternatives to single occupancy vehicles. Foursquare ITP collaborated with GWRideConnect’s leadership to update the agency’s vision, mission, goals, and objectives. To inform our recommended program enhancements, we conducted stakeholder interviews and user focus groups, both online and in person, as well as a peer review to evaluate industry best practices. We proposed strategies to facilitate GWRideconnect’s organizational and programmatic expansion, including a constrained and unconstrained financial plan and performance measurement metrics.