I examine how security analysts’ prior expertise influences the complexity of their evaluations in the context of a new technology. Drawing from research on managerial cognition, I argue that analysts with prior experience or status engage in schematic information processing that affects the complexity of their evaluations. Further, I develop the construct of evaluative complexity, which is an indicator of comprehensiveness of analyst evaluations. Historical data from the early internet industry (from 1995 to 2005) of approximately 1800 analyst reports on the initial public offerings in the internet industry support my predictions that analysts with either prior experience or status demonstrate less complexity in their evaluations of internet firms. Specifically, in new technology contexts experienced or high-status analysts are more likely to assess new technological firms from unitary perspectives and convey more certainty in a context that calls for caution. My research aims to contribute to our understanding of the role of infomediaries in the emergence of new technologies and the paradox of experience and status in these contexts.