This paper considers the impact of the current generation of automation technologies on determining compensation and hiring trends of entry level legal professionals over the past decade. Analysis is conducted through qualitative interviews of legal professionals as well as regression analysis of occupational and wage data from the Bureau of Labor Statistics. Amidst academic speculation as to what role the future of AI technologies will have on the job market, this paper hypothesizes that in the face of more and more capable automation technologies, compensation and hiring of entry level legal workers has decreased relative to the rest of the legal field. The empirical results fail to produce statistically significant evidence of this relationship, but along with the results of the interview process, point towards an emerging trend of decreased need for legal support.