The proposed tool will provide users with a platform to access a side-by-side comparison of classroom assessment and job posting requirements. Using techniques and methodologies from NLP, machine learning, data analysis, and data mining: the employed algorithm analyzes job postings and classroom assessments, extracts and classifies skill units within, then compares sets of skills from different input volumes. This effectively provides a predicted alignment between academic and career sources, both federal and industrial. The compilation of tool results indicates an overall accuracy score of 82%, and an alignment score of only 75.5% between the input assessments and overall job postings. These results describe that the 50 UNT assessments and 5,000 industry and federal job postings examined, demonstrate a compatibility (alignment) of 75.5%; and, that this measure was calculated using a tool operating at an 82% precision rate.