To achieve the complex and multidimensional goals of community wealth creation and resilience, communities of all sizes and types are using a variety of planning processes. In this chapter we explain how the Environment, Community, Opportunity and Sustainability (ECOS) Project, for Chittenden County, Vermont, USA is a model for developing and implementing a cross-sector planning process informed by knowledge drawn from community engagement and a community indicators program. This case study provides a model for partnering a regional planning entity with academic and research institutions, federal, state and local government agencies, economic development organizations and the private sector. The resulting sustainable, living regional plan was created with input of over 60 institutions and 600 community members. We specifically focus on facilitating community engagement and the development and implementation of the community indicators program. We conclude with lessons learned and strategies for improving the effectiveness of partner relationships and communicating complex regional planning and community development projects through a collective impact framework.