This 10 year overview of a citywide program implemented to improve the quality of childcare and education in San Francisco provides a description of critical issues related to implementation of an assessment process as well as factors that influence success related to initiating and sustaining quality improvement efforts in early care and education (ECE). The population of interest included all licensed childcare programs and family childcare homes in the city and county of San Francisco receiving public funding and those serving families with subsidies. The assessment tool chosen by city childcare leaders was the Environmental Rating Scales (ERS) for preschool, infant toddler and family childcare sites. Quality improvement plans were developed based on the results of the assessment of each classroom or family childcare home, followed by technical assistance targeted at improving the quality of the environment and teaching practice. Because assessment scores are currently tied to city funded subsidies, motivation for participation in the program becomes a critical factor for those programs that depend on the subsidies. Lessons learned can support other endeavors to improve the quality of childcare and education and include engaging ECE teachers in intentional dialogue that results in internal motivation to improve the quality of their teaching, along with systemic supports that include teachers, families and funding streams to sustain quality care. (author abstract)