Drawing on a qualitative case study of four Head Start sites, this article analyzes a number of governing patterns that have emerged and grown in the field of early childhood education and care in the United States. This article specifically highlights a government's enhanced oversight and management of Head Start programs by mandating a school readiness data system in their local programs: establishing a set of measurable school readiness goals, and collecting and analyzing ongoing child assessment data to monitor children's progress in meeting these goals. The primary focus of this article is to illustrate the experience of Head Start teachers and children with a commercial online child assessment and record keeping system called the "Teaching Strategies Gold." Research findings of this article suggest that seemingly "authentic, ongoing observational system," Teaching Strategies Gold actually extends and intensifies the techniques and effects of power operating on both children and teachers on a more minute and everyday level. It (re)shapes the conditions of work and constructs new norms for teachers themselves as "ongoing" assessors/observers. Pressure to "collect" all the required observational evidence that would also determine children's progress toward the next higher level has dramatically changed the nature of free play and small group activities into more "functional," "hierarchical," and "analytical" space.