Maintaining satisfaction and retention among the commission-based sales space presents a conundrum for managers and employers. This analysis address factors relating to commissions and income; experience; work environment; education; or gender and how each contributed most significantly toward maintaining strong levels of satisfaction and retention among commission-based industry space. The research method utilized a survey questionnaire of sales representatives in the medical sales industry (n=91), along with interviews and narrative analysis. The survey approach examined satisfaction levels vis-à-vis income and demographic aspects. While income was a predictor of satisfaction, surprisingly, years of time in the industry proved a greater a predictor of satisfaction levels on the job. Those sales representatives with under two-years of experience in the industry proved to be the least satisfied of all representatives surveyed. This outcome likely stems from the difficulty in initial build-up time that its takes to create the sales pipeline and find success selling in an industry.