Natural Language Processing (NLP) is a branch in data science that marries artificial intelligence with linguistics. Essentially, it tries to program computers to understand human language, both spoken and written. Over the past decade, researchers have applied novel algorithms to gain a better understanding of human sentiment. While no easy feat, incredible improvements have allowed organizations, politicians, governments, and other institutions to capture the attitudes and opinions of the public. It has been particularly constructive for companies who want to check the pulse of a new product or see what the positive or negative sentiments are for their services. NLP has even become useful in boosting sales performance and improving training. Over the years, there have been countless studies on sales performance, both from a psychological perspective, where characteristics of salespersons are explored, and from a data science/AI (Artificial Intelligence) perspective, where text is analyzed to predict sales forecasting (Pai & Liu, 2018) and coach sales agents using AI trainers (Luo et al., 2021). However, few studies have discussed how NLP models can help characterize sales performance using actual sales transcripts. Thus, there is a need to explore to what extent NLP models can inform B2B businesses of the characteristics embodied within their salesforce. This study aims to fill that literature gap. Through a partnership with a medium-sized tech company based out of California, USA, this study conducted an experiment to try and answer to what extent can we characterize sales performance based on real-life sales communication? And in what ways can conversational data inform the sales team at a California-based mid-sized tech company about how top performers communicate with customers? In total, over 5000 sentences containing over 110 000 words were collected and analyzed using two separate rule-based sentiment analysis techniques: TextBlob developed by Steven Loria (2013) and Valence Aware Dictionary and sEntiment Reasoner (VADER) developed by CJ Hutto and Eric Gilbert (2014). A Naïve Bayes classifier was then adopted to test and train each sentiment output from the two rule-based techniques. While both models obtained high accuracy, above 90%, it was concluded that an oversampled VADER approach yields the highest results. Additionally, VADER also tends to classify positive and negative sentences more correctly than TextBlob, when manually reviewing the output, hence making it a better model for the used dataset.