The Yale Alumni Association’s (YAA) strategic imperative is to increase constituent engagement and satisfaction through personalization. In this context, Yale engaged Next Generation’s Phil Goldstein for organizational effectiveness consulting, assessing the structure, staffing, and processes for customer service and help desk support to alumni and volunteer leaders. Outcomes included design of a structure and staffing model to improve service, increase adoption of digital solutions, and enable the organization to use data to create improved online experiences. Proposals to alter staffing were made in the context of the strategy and programmatic changes YAA is pursuing to deepen alumni engagement. Recommendations included strategies to leverage technology to facilitate more efficient alumni support without losing the personal touch.