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.